Wikipedia talk:WikiProject Chemicals/Archive 2009

Archived discussion of WT:CHEMS in 2009

Name of glucose 6-phosphate

I was just looking at Glucose-6-phosphate. Although I'm pretty ignorant about biochemistry, it seems to me that the correct name should be Glucose 6-phosphate (only one hyphen), because the phosphate is a separate word from the glucose. Is this the case? You can also see other pages like Fructose 6-phosphate. Should the page be moved? Walkerma (talk) 20:45, 31 December 2008 (UTC)

Yes, checked with IUPAC, the page should be moved, and I've just done it! Physchim62 (talk) 19:10, 1 January 2009 (UTC)

Thanks! Walkerma (talk) 18:18, 2 January 2009 (UTC)

Citations

When citing journal articles is it advisable to use text citations or link to the online journal if avaiable? Tpepper88 (talk) 15:08, 1 January 2009 (UTC)

Fill out {{cite journal}}; diberri's tool can fill it out for you, given a PMID. --Rifleman 82 (talk) 17:15, 1 January 2009 (UTC)

Happy New Year

And the very best wishes to you and your families. Wim van Dorst (talk) 22:43, 1 January 2009 (UTC).

Soluability in water, in the Chemical Infobox

I was trying to get a relative feel for how melamine compards to TCE (the dry-cleaning agent that has contaminated lots of ground water, due it it's low soluability). The Melamine page [1] infobox lists its soluability as: Solubility in water 3.1 g/l (20 °C)

The infobox for trichloroethylene on it's page (http://en.wikipedia.org/wiki/Trichloroethylene) lists soluability as: Solubility in water 0.015 g/100 ml (20 °C)

It would help if there were consistency here...g/l. The math isn't hard, but at least keeping to the SI multiples [2] would help. Russella (talk) 20:43, 3 January 2009 (UTC)

CAS Verification

There's a nice list of chemical compounds with incorrect CAS numbers on Talk:List of CAS numbers by chemical compound, if anyone wants to help out with correcting them. shoy (reactions) 18:44, 10 January 2009 (UTC)

Adams' catalyst

Should we move this article to platinum dioxide or platinum(IV) oxide? I'm asking, because it appears that the catalyst is a pure compound, unlike Raney nickel or Lindlar catalyst, which are not. So, either name might be more obvious than the current one. --Rifleman 82 (talk) 18:51, 10 January 2009 (UTC)

No. Unless someone corrects me (I have been known to be wrong in the past ;), Adam's catalyst is a catalyst prepared from platinum dioxide, not a pure phase. Commercially, PtO₂ is (often) sold as "Adam's catalyst" because that is its major use. I think we need to be very careful in not mixing the two terms. It seems to be an analogous situation with Raney nickel, where there is confusion among (non-)specialists about the nature of the catalyst, but in which the catalyst itself is obviously notable. The solution would appear to be to create a stub for the pure compound. Physchim62 (talk) 19:17, 10 January 2009 (UTC)

Heterogeneous catalysts are almost always "witch's brews" and Adams' catalyst is no exception. --Smokefoot (talk) 20:51, 10 January 2009 (UTC)

Hydronium

Hydronium has shown up at WP:RM to be renamed to Hydroxonium and subsequently redirect to the Hydron article. See Talk:Hydronium 76.66.198.171 (talk) 22:32, 10 January 2009 (UTC)

Hydrogen anion vs Hydride

What do others think about these two? If hydrogen anion = hydride, then the former short article (which has some good content) might be merged.--Smokefoot (talk) 00:02, 12 January 2009 (UTC)

articles which say "insoluble"

Probably a bunch of false positives on the list, but these articles list the solubility (in water) of these substances as insoluble. In my opinion, this should be replaced with either the really small solubility rate or the solubility product constant. —harej // change the rules 04:15, 12 January 2009 (UTC)

In my opinion, "insoluble" is acceptable, though not ideal. In many cases, the solubility data may not be available or very difficult to find. Is it worth the effort to find the data only to replace a zero with a number very close to zero? -- Ed (Edgar181) 13:10, 12 January 2009 (UTC)

In any case, where did that list come from? how was it obtained? There are so many errors on it that it seems useless for any real curation. Taking a couple of obvious false positives (copper(II) chloride and Copper(II) sulfate), I can't find any evidence of them having been described as insoluble in the recent past. Otherwise, I agree with Ed that there is little to be gained by replacing "Insoluble" with a very small number which we might not even know. Physchim62 (talk) 16:16, 12 January 2009 (UTC)

It came from a sloppy cross section of articles that use the chem box and a Google search for "insoluble". Yep. —harej // change the rules 19:59, 12 January 2009 (UTC)

Uhs (167) - Ust (173)

See Wikipedia:Articles for deletion/Unhexseptium. Elements 167 to 173 have been sent for deletion as pure speculation. Note that even the chemical properties cannot be predicted, since some theories say that no electrons can be added to the electron shells beyond 139. 76.66.198.171 (talk) 00:49, 16 January 2009 (UTC)

Paracetamol at FAR

The synthesis section has no references and appears educational rather than industrial. Could someone more knowledgeable improve it? Xasodfuih (talk) 12:43, 17 January 2009 (UTC)

Two points to remember:

1. The synthesis of paracetamol is a "classic" introductory organic preparation (see examples from universities in India, Malaysia, Fiji and Saudi Arabia). An appropriate reference would be here
2. The acetylation of 4-aminophenol with acetic anhydride is one of the industrial methods for producing paracetamol (see GB 1469099), although this site suggests that there are others.

Physchim62 (talk) 15:41, 17 January 2009 (UTC)

Perhaps Smokefoot might be able to dig out Ullmann's? --Rifleman 82 (talk) 05:22, 20 January 2009 (UTC)

List of chemical compounds with unusual names

List of chemical compounds with unusual names has been nominated for deletion. 76.66.198.171 (talk) 05:24, 23 January 2009 (UTC)

It should be noted that a centralized discussion of "Lists of unusual things" is taking place at Wikipedia talk:Centralized discussion/lists of unusual things. shoy (reactions) 19:01, 28 January 2009 (UTC)

Large numbe of style chages from IP Special:Contributions/70.137.173.82

Frankly I don't like that he made the diagrams smaller. Nor do I see a need to insert spaces in chemical names in text. I can see the need for line wrapping in infoboxes, but even that is suboptimal given that we have Template:Wbr. I guess he was using a mobile client. Xasodfuih (talk) 22:55, 25 January 2009 (UTC)

• Spacing in names of chemicals compounds should be ruled by chemistry rules, and not by linewrap thoughts. Recommendations on names can be found in the the style guide. Wim van Dorst (talk) 23:13, 25 January 2009 (UTC).
  • I don't see this issue discussed there. User:CBM pointed out to me that my initial version of Hyodeoxycholic acid had a screen-wide infobox in his undisclosed browser due the IUPAC being rendered on one line. I haven't experienced the problem myself, but using browser-compatible non-breaking space in the infobox (which wbr is inserting) seem entirely reasonable. I don't see the need to do this in the prose though. What about picture width? Is there guideline somewhere that it needs to be 200, not 240px now? Xasodfuih (talk) 23:19, 25 January 2009 (UTC)
• This is just the latest in a periodic spate of such whitespacings. I haven't seen any consensus for inserting spaces into long chemical names, and I suspect especially for the inboboxes it could interfere with searching/scripted data processing of these pages. Long strings are a rendering/layout problem that we do need to resolve if it can be done without damaging the content (concur with Wimvandorst). I'm less concerned with body-text, since that's not as technical-data as the infoboxes, but if we're gonna solve this, let's really solve it. Completely forgot we had a somewhat portable template solution! Regarding the images, the infoboxes themselves are fixed-width and have a default image-size. Making them smaller than the box is already seems fairly pointless from an overall-layout perspective. If the problem is "images are generally too large", then we need a new consensus on the default size. Further, it's pointless to hard-code a size that's the same as the chembox default, which is what IP appears to have done for the cases I spot-checked. Something's either weird in the box display on certain browsers or else in IP's settings. DMacks (talk) 23:22, 25 January 2009 (UTC)
  • The name wrap in the drugbox seems to work fine for me (in IE and Mozilla) without these extraneous spaces. Physchim62 (talk) 23:32, 25 January 2009 (UTC)
  • I thought the name wrapping problems of old browsers was solved. From then onward, I really dislike the use of any method (including hard whitespace, html breaks, or templates such as wbr) that messes up with the proper spelling of long words, such as chemicals names. (ps drugboxes and chemboxes are fine in FF too). (pps. There's an explicit draft text now in our style guide) Wim van Dorst (talk) 23:44, 25 January 2009 (UTC).
    • Where exactly? The only mention of "space" is in "There is no space between the end of the element name and the opening parenthesis: hence silver(I) fluoride not silver (I) fluoride. Note that this is an exception to the usual English style for parentheses." "White" does not appear on that page. Xasodfuih (talk) 23:55, 25 January 2009 (UTC)

• Xasodfuih asked me to provide more details about my problem with the Hyodeoxycholic acid article. The chemical name is poorly wrapped by Firefox 2.0.0.18. Here is an image of the rendering I see with this browser: [3] (note this has been reduced to 75% of its original size). The full build ID of the browser used to make that picture is "Mozilla/5.0 (X11; U; Linux i686; en-US; rv:1.8.1.18) Gecko/2008103000 Iceweasel/2.0.0.18 (Debian-2.0.0.18-0etch1)". I have also seen the same wrapping problem on another computer running Red Hat Enterprise Linux 4, which uses a different Firefox in the 2.0 series. The problem does not occur with Firefox 3.0.5. — Carl (CBM · talk) 02:15, 26 January 2009 (UTC)
  • I can verify the same problem in Doxycycline in Firefox 2.0. Apparently this a common issue in Mozilla-derived browsers (and firefox 2.0 is not an archaic browser). Possible ways to resolve the problem include adding spaces or setting overflow: auto on the table cells. The latter is what the devs did for diff viewing in Mediawiki. — Carl (CBM · talk) 02:45, 26 January 2009 (UTC)
    • I used break tags for this purpose for a very long time and was never reverted/taken to task for it. I stopped doing so only when names started wrapping automatically in my browser; apparently, it still doesn't work for everyone. If this can be solved directly in {{Drugbox}} and {{Chembox}}, then we should implement it quickly. If it can't, I don't think we should discourage these "palliative" methods. Fvasconcellos (t·c) 13:24, 26 January 2009 (UTC)
      • I have to concur with Fv. People have been adding spaces and "<br>" into the middle of IUPAC names and SMILES strings for years. It's been a common workaround for the browser display problem, so 70.137.173.82 shouldn't be faulted for doing it. The ideal solution of course would be to adapt {{chembox}} and {{drugbox}} to handle long strings differently (but that's easy for me to say because the work will have to be left up to someone else with much more technical knowledge of these types of things than me). -- Ed (Edgar181) 13:57, 26 January 2009 (UTC)

Messages pasted from my talk page re: Your rollback hyodeoxycholic acid

I've moved the discussion here because I'm not the one to unilaterally make this decision. Also I find the tone and the amount of posts on my talk page unhelpful. Xasodfuih (talk) 13:27, 26 January 2009 (UTC)

You have rolled it back to a version which still contains manually inserted breaks, however at illogical places. it is x,y-dihydroxy-
y,z-dimethyl etc. Not x,y
-dihydroxy-y,z
-dimethyl. And I fixed it such that it is logically coherent. Now in your rollback it looks like written by a chemical illiterate and still has manual wrap in it. revert to my version, that is better. trust me. also you rolled back insertion of reflist 70.137.173.82 (talk) 09:05, 26 January 2009 (UTC)

The illiterate version, as you call it, was inserted by a mathematician (User:CBM); nobody besides him and you had problems with the infobox. I for one could not care less where the line breaks happen in the IUPAC name. Also, I don't see why you're wasting your time changing one reflist syntax to another when they both work equally well. How about writing an article? Xasodfuih (talk) 09:10, 26 January 2009 (UTC)

I am mathematician myself, but also had chem classes. The arrangement as edited in my revision facilitates reading. reflist allows a centralized update of the reference list format in the reflist macro, should the need arise. I have done major proofreading and editing on many articles (look at temazepam and discussion), only you can't see it, because I have variable IPA 70.137.x.x. 70.137.173.82 (talk) 09:17, 26 January 2009 (UTC)

Two days you said you were an electrician. Xasodfuih (talk) 09:49, 26 January 2009 (UTC)

Yes. grad engineer EE, followed by classes in math (extended) and some chem classes. working in R&D since 70s. But I can still solder. My main field was systems and algorithms, systems architect of semiconductor circuits. Now retired. That kind of electrician. 70.137.173.82 (talk) 10:09, 26 January 2009 (UTC)

And the illiterate version still contains manually inserted breaks. The spaces I used give the display algorithm more freedom to adjust as sees fit. If you remove the still present breaks it pumps up the box to huge size. 70.137.173.82 (talk) 09:21, 26 January 2009 (UTC)

Maybe there is a reason that CBM and me as mathematicians have problems with your chem box? (even if I find my layout more logical than his) I suspect the problem cannot be fixed in the chembox script. 70.137.173.82 (talk) 09:26, 26 January 2009 (UTC)

Seems like the reason is that mathematicians use Unix and the browsers available for it, or firefox. The problem does not show up on IE6. IE6 seems to recognize the dash, the brackets and square brackets as separator characters for word wrap. FF 2.x does not. 70.137.173.82 (talk) 10:01, 26 January 2009 (UTC)

I'm using FF 3.x and it has no problems breaking those lines. Time to upgrade? Xasodfuih (talk) 10:06, 26 January 2009 (UTC)

Can't upgrade on my home computer, 64Mb win98. Not supported by ff3. No money for something better. fixed income, retired, no need for systems architects, main problem of selling an old fart in silicon valley, with so many cheap youngsters around. 70.137.173.82 (talk) 10:16, 26 January 2009 (UTC)

Did a line wrap experiment on chenodeoxycholic acid. This displays totally garbled on ff2.x, not very nice but wrapped around in ie6. with spaces inserted it displays very nice on both. ff3 I could not try, you know. You have to care for the least common denominator of browsers out there. So it ABSOLUTELY has to work with everything, thats how portable texts work. Think of other nonPC clients as well. So you will need to fix that, you can't say BAAH, time to upgrade, thats what I am telling you as a professional.

p.s. Hard to work with you, people. You think everybody else is a charlatan. Never came to your mind what you can potentially study until your 60s? Yes you can be electrician and mathematician at the same time in the 5th decade of professional work and study. 70.137.173.82 (talk) 11:01, 26 January 2009 (UTC)

You have to count, that I worked since '64, in a radiation counter lab, in factory for electrical motors, in a factory for nautical instruments. Took evening classes. then full time study, grad engineer EE degree in spring '69. Part time R&D lab electronics, classes math, physics, chem, to my taste. First patent in the 70's. Entered full time industry position '75. Participated in first attempts of digital video processing '78. Electrical filtering, first large LC filters, with their specific mathematical methods of synthesis (See "Cauer, Theorie der linearen Wechselstromschaltungen") now moving focus to digital filters. Highly mathematical construction problem. First projections of microcoded digital signal processing, but several technology generations away from feasibility. Integrated solutions hardwired feasible before the generalized programmable approach. Endless detail work. Nonlinear optimization as a design tool. Variants of modified Gauss-Newton, Levenberg Marquardt methods, attempts to make it foolproof stable as design tool. (You know, the approximation of frequency domain constraints with time domain /transient response requirements) Seeking compromise between group delay and amplitude reqs in all-pass free systems. Heavy simulation problems, the upcoming era of register transfer languages to get behavioral and cycle-accurate simulations of digital signal processing. Building of compilers for such RTL, mixed with gate level blocks. Pseudocode generation, true machine language generation, attempts to push primitives down to microcode. Microprocessors developing, single chip controllers. Many problems with video speed converters, particularly testability. Much need for mathematical approaches, stuck-at model. Howto. No commercial testers available, helping out with factory automation. Son-do-all solves much of it. Upcoming electronic identification cards, security processors, building of new instruction set architectures for embedded and security and embedded security. It becomes feasible to pack a PDP11 class processor in a credit card, and he knows your finger print and two-factor authorization, RSA, Diffie-Hellman. Finally microprocessors have reached the speed for digital video processing, the old ideas from the seventies about programmable and microprogrammed video solutions have punched through the time-wall and become feasible. They were all infeasible through 25 years. Dreams become real. I participate at the fringe of such development and see my old dreams taking on a LIFE of its own. On the other hand the credit cards with a security processor become feasible and a commodity, they are to go into passports. What was NSA classified security processors for 300k$ is now a commodity for dollars and in your pocket without you even knowing. Now they will move into secure cell phones, which also pay your bills. A soapbox compresses video into a format for your Ipod. Analog TV superseded. No need for me any more, the problems are solved. And you ask me (in a squawky suspicious voice, I presume?) if I am now an electrician or a mathematician? Because I say so one day and different the next day? Sure I lied, what? Want to give me a job, or just curious? Want my resume and hire me? Or do you want to pull off the same stunt yourself? Now I am curious. 70.137.173.82 (talk) 12:33, 26 January 2009 (UTC)

So I propose you stop bickering now, and recognize we have a problem with the display of long iupac, on browsers we have to realistically support. I propose to allow dash space, bracket space etc etc as iupac elements to facilitate readability and auto wrap. No chance that we all have to upgrade to ff3. Also consider display behavior on other clients, aim for portable text and the least common denominator. I have a grudge against so many people like you, who are jumping to conclusions immediately and act on a hunch and on a consensus of two, and then they become fidgety and insolent and try to block dissidents. 70.137.173.82 (talk) 13:14, 26 January 2009 (UTC)

block him, heeelp, block him fast, an emeeeergency, heelp, we have a vandaaal!. But first argue the case with me. 70.137.173.82 (talk) 13:18, 26 January 2009 (UTC)

OK, my 2p here. Although not very often, those names are terms which might be searchable. And "search term", "search-term", and "searchterm" are three different things (though google may come up with all three results, bit depending on how good the algorithm is). Hence, extra spaces or other format modifiers should NOT be added to that field, the name should be correct. With our current drive to getting these boxes to contain verified data, that should be even stronger.

Now I understand that there are some people on 'strange' browsers (or relatively old versions) who can't upgrade to the newer version. That is a problem, and we need to see a) if we can use settings (somewhere, including site-wide) to go around that problem. I don't think we should go through the whole set of chemboxes changing that field, and even if there are no other solutions, I would not change that field, but maybe choose the option as we have with the InChI (all in all, we hardly need to see that name, especially when it is relatively long). --Dirk Beetstra ^{T C} 15:02, 26 January 2009 (UTC)

I propose to squeeze blanks after separators out before searching. iupac is anyway ambiguous in many ways and the blank is after another separator character nonfunctional. (but not without a separator, like in acetic acid ethyl ester) (where separators are ()-[],. ) 70.137.173.82 (talk) 15:31, 26 January 2009 (UTC)

Now you are proposing a software feature .. until that time, please don't add spaces. Thanks. --Dirk Beetstra ^{T C} 15:34, 26 January 2009 (UTC)

I have reverted all edits/removed all spaces in the edits by 70.137.173.82. They can always be undone if there is consensus to have the spaces there (but seen there are many people who have troubles with the edits in some way or another, I think this is the best starting point for a discussion). --Dirk Beetstra ^{T C} 15:39, 26 January 2009 (UTC)

klei me an mors. bedankt. 70.137.173.82 (talk) 16:07, 26 January 2009 (UTC)

re stylechanges by anon 70.37.x.x

The blanks I have inserted for following reasons: Long names in the drugbox/chembox do not wrap, but stay one line and then increase the width of the box to huge dimensions, displacing the text and making the article unrreadable on smaller display width. The problem occurs if you have "sidebars" enabled on firefox, or in std display mode in IE. If you use automated search of the iupac name. then dash space should be compressed. The "zero width space" is less portable, as it is not ascii character set. Please switch sidebars on in your browser, and observe how the box displays, and other problems. The you see what I did and why. This are not really style changes. The box really blows up in size on very long names. And you HAVE a problem, which I tried to solve. 70.137.173.82 (talk) 02:50, 26 January 2009 (UTC)

See screenshots by Carl, above. Yes that is the problem, and is worse on narrow or variable width display, i.e. with sidebars enabled. You simply can't read that. 70.137.173.82 (talk) 03:22, 26 January 2009 (UTC)

This problem shouldn't be solved by attempting to insert breaks manually. Therea re 5000 chembox pages alone. Apart from being more elegant, it's more practical to keep formatting the way they are, and fix the box. --Rifleman 82 (talk) 03:25, 26 January 2009 (UTC)

Until then, 70.* should not continue to add line breaks which will only have to be reversed when the box is fixed for FF2. --Rifleman 82 (talk) 03:26, 26 January 2009 (UTC)

He appears to have thoroughly ignored this message, so I asked for him to be blocked on WP:ANI. Xasodfuih (talk) 07:25, 26 January 2009 (UTC)

IUPAC names at Diberri's tool:

I mentioned that I didn't trust the IUPAC names by PubChem, which Diberri's tool generates. That's just my opinion; does anybody else encounter unreliable names? Discussion at User talk:Diberri/Template filler. --Rifleman 82 (talk) 03:37, 26 January 2009 (UTC)

Icosa vs eicosa

The same 70.137.173.82 user changes icosa to eicosa. Is there a wiki standard for this? (See also IUPAC_numerical_multiplier#Icosa-_v._eicosa-). Xasodfuih (talk) 07:40, 26 January 2009 (UTC)

I see that icosa is preferred over eicosa, even if Beilstein uses eicosa. So ok. make it icosa, if that is the consensus. Overexcited quick hands please chill out. You see below that the same issues with display recognition of separator characters is pending for the drugbox for quite some time, without an answer. see below. So I would call your blocking request for my best efforts to make pages display nice a bit quick and insolent, young editor. Blocking is appropriate for vandalism, not for good faith best efforts. And you have reverted me, before even asking for reasons. Also I have not seen a response to my part of the discussion. 70.137.173.82 (talk) 08:46, 26 January 2009 (UTC)

Drugbox

See also here http://en.wikipedia.org/wiki/Template_talk:Drugbox#Line_wrap_in_IUPAC_names

the drugbox has the line wrap problem too with firefox 2.x 70.137.173.82 (talk) 04:01, 26 January 2009 (UTC)

External links to ESIS

We, the de-WP chemistry project, got aware that ESIS does not allow direct external links to its database any more. Hundreds of articles are affected (e.g. try the EC number link in Ethane). There is an on-going discussion in the de-WP chemistry project. We got the following e-mail reply from the responsible IT Project Manager:

“Personally I do not use wikipedia, so I do not know what is there linked to ESIS. Anyway, what I know is that normally before making direct link to our databases there should be a request from the user. What I know also is that numbers of spammers are using ESIS, and also because based on php languages some features have been disallowed and only requests using the form are available.”

So, probably, we should make a request for direct linking to the ESIS database. --Leyo 15:03, 27 January 2009 (UTC)

Is the EC number issued/owned/(something like that) by ESIS? --Dirk Beetstra ^{T C} 15:59, 27 January 2009 (UTC)

See EC number (chemistry). --Leyo 16:10, 27 January 2009 (UTC)

http://ecb.jrc.ec.europa.eu/esis/index.php?GENRE=ECNO&ENTREE=200-814-8 does not work (any more) if you click it, but it works with copy/paste into the browser. --Leyo 17:23, 27 January 2009 (UTC)

I can't see what their problem is? Spammers? Data-miners, possibly! Still, they control the means of access under the Database Directive, as the only legal requirement under REACH is that the data be made public. I would support any formal request to allow deep-linking from *.wikipedia.org sites. Physchim62 (talk) 17:38, 27 January 2009 (UTC)

ESIS now allows de-WP to link directly to its database entries so far (see their reply). --Leyo 23:42, 3 February 2009 (UTC)

It's OK now. --Leyo 14:56, 10 February 2009 (UTC)

Yes, I tested it by accident last night and it was working from enwiki as well. Thanks for all your work on this one, and freundlichen Grüssen to our German colleagues! Physchim62 (talk) 15:36, 10 February 2009 (UTC)

It seems that there were (unknown) problems in the past with Wikipedia and ECB de:Wikipedia:RC#Antwort_IV. We are trying to mediate the case and establish a relationship for the future. Matthias M. (talk) 20:19, 23 February 2009 (UTC)

Problem with wide infoboxes seems better

I noticed some edits to {{Chembox IUPACName}} so I made another screenshot of Hyodeoxycholic acid. The problem with the long name and firefox 2 seems to be fixed: [4]. The width of the infobox does not change when I click on "show" to see the chemical name; the table cell grows a horizontal scrollbar instead. Note that for most pages the cache has to be purged (either by making an edit, or using action=purge) before the changes are visible. Thanks, — Carl (CBM · talk) 16:15, 27 January 2009 (UTC)

Thanks for the testing, Carl. This seems a good solution, and not just an interim one. Hiding the IUPAC name by default seem a good idea in a general encyclopedia. I doubt that most readers learn anything from it, and it makes the infobox longer by a few lines for complex compounds. Xasodfuih (talk) 16:36, 27 January 2009 (UTC)

look at Violaxanthin. 70.137.173.82 (talk) 21:36, 27 January 2009 (UTC)

The alternate names in pharmacists/nonsystematic/pidgin language and hybrids thereof with iupac may also be pretty long and pose the same problem of line wrapping as the iupac names. 70.137.173.82 (talk) 21:41, 27 January 2009 (UTC)

Yes, but the problem with Violaxanthin isn't with the name, it is with the size of the image! Someone has set the image to 375px, instead of the 250px it used to be, so of course the box is too wide! Physchim62 (talk) 21:44, 27 January 2009 (UTC)

In articles like Violaxanthin, wouldn't it be better to put the wide image in the article text and but a "see text" message in the infobox?

Ben (talk) 21:54, 27 January 2009 (UTC)

In any case, there is not the same problem with Violaxanthin in firefox 2. Here is a screenshot after I removed the soft spaces: [5]. It looks like the "other names" box max also need to be condensed on that one, and the image is quite wide. I would be grateful if someone could check that the chemical names are still correct. — Carl (CBM · talk) 22:14, 27 January 2009 (UTC)

The problem still does occur with HU-308 which uses {{drugbox}}. — Carl (CBM · talk) 22:16, 27 January 2009 (UTC)

Violaxanthin: changed image to 250px, removed one remaining 200-character zero width space; strange there was a double dash leftover in the first alternate name; will check against earlier version. But indeed now the length of the alternate name is the limiting factor, expanding the width of the box. 70.137.173.82 (talk) 22:25, 27 January 2009 (UTC)

Carl, checked against earlier version and reinserted a beta in beta carotene, which got lost in editing. Now definitely the alternate name is the limiting factor. The list of the many alternate names is any way separated by manual breaks. So, how much does it make sense to forbid manual breaks in the names in this list? I hope we don't end up hiding all cells of the drugbox, bringing them up only on a push of a button with a scrollbar. ;-) 70.137.173.82 (talk) 22:39, 27 January 2009 (UTC)

I think the scrollbar makes long names rather hard to read.

That "only few users" look at iupac or other "long chemical names" in pidgin is a conjecture.By showing only a window into the name, the scrollbar tool takes on the character of an aid for the blind itself.

Unfortunately an all too popular version of the articles reduces the text body of chem articles to "is toxic, EPA classes, drug schedule, causes dependence and brain rot, if forbidden and bad for the environment and is the result of the pharm industry conspiracy" reflist: the list of superfund sites and naturopathic alternatives, as well as chinese toy incidents, and if applicable list of police chemist publications, NIDA publications and coroner reports, as well as scare stories in leaflets by the grass roots movement of concerned school teachers, parents, soccer moms, and sheriffs organizations and related evening news and newspaper articles. 70.137.173.82 (talk) 06:50, 28 January 2009 (UTC)

Side-scrolling and hide/click-to-reveal are independent features. Easy to make it hidden-by-default but when displayed be unscrolled (i.e., widen the infobox as necessary). That would solve the objection that the IUPAC name needs to be seen by the general public and that scrolling is a crutch for them (that's two conjectures there!) rather than a way to make a long string totally searchable and selectable for cut'n'paste as a correct string. Your hyperbole aside, for many chemicals, the lay public probably doesn't care at all about technical all details anyway...it's not useful or interesting unless you're doing science or something else technical, in which case it's pretty important that the technical details be as correct as possible. The real dilemma here is "correct in fact" and "displays with pleasing layout" cannot both be accomplished...we've gone from "correct but terrible layout on some browsers" to "correct and usable layout on all browsers". Given the kind of information this is, I'm not willing to go "less than correct and prety good layout on all browsers". Note that even with the whitespace-added solution, the layout isn't great...there are all these weird whitespaces in the middle of the name! DMacks (talk) 07:21, 28 January 2009 (UTC)

Whitespaces inserted after "separator characters" like dash would not change the semantics and therefore not the correctness in fact. If done appropriately it would look better than the auto wrap on new browsers. I don't talk about inserting spaces behind every separator, but in appropriate places, e.g 3,7-dihydroxy-(blank)4,6-dimethyl-(blank)longblah-(blank)otherlongblah. The main issue is machine readability by search engines and other tools, e.g. reading aids and indexing algorithms. Besides where I live around 60% of the people have at least a bachelors of science/ engineering/technology. 70.137.173.82 (talk) 08:41, 28 January 2009 (UTC) 70.137.173.82 (talk) 08:49, 28 January 2009 (UTC)

Let me add that the layout problems of chemical names are the same as the layout problems of other high level languages.

Example Statement:

if Adam<=Eve then Sum:=Sum+3.7*Adam+5.1*Eve else Sum:=Sum+Adam

This allows insertion of additional blanks around separators

<=  := + * and existing (blank)

without changing semantics. But it doesn't allow ifAdam, EvethenSum, EveelseSum etc.etc. and allows free layout without breaking tokens:

if then else <= := Adam Eve Sum 3.7 5.1

without changing semantics.

Such free layout can be automatically reverted to the original Example statement, for machine processing, by applying lexical processing. 70.137.173.82 (talk) 09:35, 28 January 2009 (UTC)

There are a couple of 'problems' with having the spaces there, some quite big, some smaller:

• It breaks the searching using the wiki search engine: Indole-3-acetic acid, Indole- 3- acetic acid (the first hit is still the correct compound, but from result 2 everything is different); searching on Indole-3-aceticacid does not give any reasonable results.
• Using the Google engine results in practically the same information: Indole-3-acetic acid vs. Indole- 3- acetic acid
• Having the spaces may give problems with screen readers, but having a long weird name there visible may give similar problems. It would be interesting to know how people who use screen readers react on this.
• Minor 'annoying' problem: Having spaces there may result in people using new browsers trying to remove the spaces, seeing that for them the display improves (as said, the spaces do look strange on some occasions), hitting save. That would mean that we have to keep on adding those spaces for those who do have problems with displaying (i.e., inserting the spaces is not a 'permanent solution'.

Possible solutions:

• The one I implemented, hiding it from view. That solves the box-width problem (in hidden view), and all search problems. Screen readers probably now also don't read the name, and people are less likely to 'vandalise' the IUPAC name (I don't mean edits like 70.137, I mean editors who think it is fun to change numbers randomly in the name, or who would play around with the spacing if it were there).
• Tweaking systems mediawiki-wide 1: trying to enforce proper display of long names in browsers that have this problem by adapting the skin. That is dependent on if the involved browsers allow such thing.
• Tweaking systems mediawiki-wide 2: let a javascript replace ALL '-' for '- ' before rendering on older browsers.
• Tweaking systems for specific users (user needs an account): which includes one of the above two solutions, but on a local user level in their own skin.
• Insert the spaces and ignore searchability, removing 1 problem and inserting others (which includes waiting until an improved processing of the data is implemented).
• Question to people who have access to the problematic browsers. Can we replace the regular dash ('-') with 'another' dash (why does the browser not wrap on the regular dash?).
• A combination of the above.

One note, unfortunately StringFunctions is not enabled on this wiki. That would allow for 'if the length of the IUPACName is bigger than # characters, then hide it and show a show button, otherwise show the whole name'. --Dirk Beetstra ^{T C} 12:02, 28 January 2009 (UTC)

Thanks for the update, Beetstra. Is it an option to request (or push for) StringFunctions to be enabled? -- Ed (Edgar181) 12:43, 28 January 2009 (UTC)

Please address the problem of a list of e.g. 5 alternate names, which are pidgin iupac and equally long. If we hide them all the chembox has no name any more. I would have favored lexical compression before searching with a chems search preprocessor. Also nothing prevents idiots from tinkering with the names by inserting tetrahydro-fuckto-cuntodole-3,6-prickolate in the mid of the iupac name wherever they want, and I have fixed similar (not as bad) cases. Changing the numbers or other items in a plausible way is more insiduous and I have fixed such as well, including misrepresentation of references. You have to protect this info in some way, violating current policy and excluding 100Mio people in need of the GED or with a slightly subnormal IQ. I believe the machine searchability is a wild goose chase, you don't even find the eicosa from Beilstein or Chem abstracts, and you don't find long string even if they are in the article. Standing in the shoes of an idiot it would be more funny to vandalize the hidden info in an insiduous way. Then surprise, surprise. 70.137.173.82 (talk) 12:52, 28 January 2009 (UTC)

To convince yourself of the wild goose chase do a wiki search on

4,5a-Epoxy-3-methoxy-17-methylmorphinan-6-one

from the hydrocodone drug box. Look at the hits: They are false drops. It turns out that wiki search looks for a hit containing epoxy, methoxy, methylmorphinan, and one. It doesn't see the 4,5a. etc. It also finds names with these components but other interspersed elements, like hydroxy etc. namely oxycodone. Look, look, in particular at the highlighted hit list and see "how" and "what" he matched. bingo. Your examples were oversimplistic and wiki search does NOT match on the full search string, but on its parsed down components. The differences between different layouts are explained by this, they are all associative search false drops. 70.137.173.82 (talk) 13:23, 28 January 2009 (UTC)

The alternative names are not very often long, there are some cases. That combined with that it is a relatively low number of editors having that problem, makes me less inclined to solve it. If it really needs a solution, put the show-button-wrapper in the value of the parameter, but don't do it for all. By far, most of them are <30 characters long.

You are right, vandalism will still occur, that is not the point. The point was the good-faith 'repairs' that remove the spaces, as for most of the editors here those spaces are simply superfluous. Protecting a agreed upon correct name is what I am working on with User:CheMoBot.

I am sorry, 70.137, we have solved the wide display of the {{chembox}] for probably >99.8% of the cases (I would be surprised if you can find more than 50 that now have problems. Applying the same to the drugbox will probably also solve most of the problems. In this case we only have to worry about people changing the name from a correct one (which is probably in most cases vandalism), and not also about those that remove in good faith the spaces. --Dirk Beetstra ^{T C} 13:33, 28 January 2009 (UTC)

Note that the chemistry and pharmacology logs provided by CheMoBot (talk · contribs) have made it much easier to catch this sort of insidious vandalism. Fvasconcellos (t·c) 14:58, 28 January 2009 (UTC)

Ok, if thats the consensus after the facts. Lets see if it is well accepted. Do you guys still think my contributions are mostly rants? 70.137.173.82 (talk) 13:48, 28 January 2009 (UTC)

CheMoBot was consensus before these facts already .. that's why we are working on that project. But I hear we have a new problem, for the browsers that have a problem with not hyphenating at hyphens, hiding does solve the problem of the wide boxes, but it appears that then in those browsers a horizontal scroll bar appears. I made another change to the template, 70.137.173.82, can you load a problem page (where you saw a horizontal scroll bar), click edit, and then preview, and then open the IUPACName? Thanks. --Dirk Beetstra ^{T C} 15:10, 28 January 2009 (UTC)

Then it increases the size of the chembox, as intended. But the chembox doesn't fit on the display area if I have sidebars on, so I see only the RIGHTMOST 60% of it. So it is truncated on the left. 70.137.173.82 (talk) 15:31, 28 January 2009 (UTC)

Besides, as you say doesn't hyphenate at hyphens, I am not sure if the dash (minus sign of ascii) is really and truly a hyphen. Besides also not confident in unicode portability for that matter, if we talk other clients. 70.137.173.82 (talk) 15:42, 28 January 2009 (UTC)

OK, that is 'fine' (better at least). Next question, are you able to copy-and-paste the whole name (in case you would need it for some reason), and are you able to click 'hide' so that the page collapses again to 'normal' (in that case you have the normal functionality of the page, I don't expect too many people who use a 'problematic' browser wanting to gaze at the IUPACName for too long;-) )?

I am also not sure if other hyphens don't give us similar problems (or possible problems) as described above. Just exploring the options. --Dirk Beetstra ^{T C} 15:57, 28 January 2009 (UTC)

If I have sidebars on, it copies the "hide" button, but only the first line of the name. The name wraps around to a second line between pentanoic and acid, as there is a blank. I have to switch sidebars of to get the full name. I think this will recur without sidebars if the non-wrapped name is wider than the display window. This is an extra problem. I begin to suspect that I have to search if I can tweak some macro in the firefox package to see hyphens as wrap points, like in ie6 and FF3.x Seemingly they changed some default setting between FF2.x and FF3. Maybe thats scriptable, I have to learn. 70.137.173.82 (talk) 16:28, 28 January 2009 (UTC)

I have ff2/OSX/x11 that easily reproduces the original layout problem (i.e., doesn't word-break on normal hyphens) and still I prefer "correct" seachability and cut'n'paste-ability. Let me know if there's anything you want me to experiment with when I get home this evening. DMacks (talk) 16:37, 28 January 2009 (UTC)

Well, we have solved the problem this far. I can't easily reproduce it under my settings, but the above questions are about it: What happens if you press 'show', can you copy the whole name (and what problems do you encounter with it), and can you access the hide button to collapse everything again back to normal. I guess 70.137.173.82 roughly gave the answer (copy-paste is a problem ..), maybe indeed some plugin or another solution? --Dirk Beetstra ^{T C} 17:01, 28 January 2009 (UTC)

See what happens if you make a chembox with a iupac string that is non=wrappable and too long to fit into the display width. Can you copy it then, what happens to the display overall? 70.137.173.82 (talk) 17:18, 28 January 2009 (UTC)

Show and hide works normal. The problem is only if the box doesn't fit in display width (in this case due to sidebar, but I guess also if the string is simply wider than display width. Not tried) Then I could do no normal copy, because I could not get to the left end of the line. 70.137.173.82 (talk) 17:27, 28 January 2009 (UTC)

That might be a hopeless case...when I asked mediawiki devs about that problem for InChI and SMILES (which do not have hyphens or whitespace at all), they recommended side-scrollable fields, which is why we did them that way (and now cloned to IUPAC). DMacks (talk) 18:20, 28 January 2009 (UTC)

Besides I got curious what other people have experienced with firefox. So I did a Google search Firefox word wrap, and got a huge bunch of forums etc. describing how you can set some Css before etc. and a list of characters etc. and then you edit this statement in a short text file and put it into some specific Chrome folder. So this kind of incompatibility with IE has been observed by others in different applications too, and has been fixed in ff3. Of course tinkering with the Chrome folder is not WP solution, where we want maximum compatibility with everything that is out there without tinkering with your computer. 70.137.173.82 (talk) 18:49, 28 January 2009 (UTC)

For smiles it should work if the line wrap recognizes parenthesis etc. as line break separator. There is an interesting character for silent hyphen something like shy, (not blushing) which you can sprinkle into strings and they wrap there. Don't know if that is portable. Don't know if FF and other browsers recognize that generally. The chem names I found are always edited with minus sign as the dash, compatible with ascii. At least If you copy from pubchem. And then FF2 doesn't recognize it but IE does. I guess if you do a copy paste from a string with embedded silent hyphens, they don't get copied, because they are nondisplaying. But again, as I have seen before with zero width blank characters, on some browsers not set to unicode they display as a grey blocks. So it is also not foolproof. But with ff2 it gives a correct wrap around with no extra spaces displayed. I think it was character 200. I was opposed to it because of the grey block issue, but maybe it is the lesser evil. 70.137.173.82 (talk) 18:49, 28 January 2009 (UTC) 70.137.173.82 (talk) 18:49, 28 January 2009 (UTC)

Quick question.

What is the IUPAC name of CsI again (Caesium/Iodine)? Thanks.Headbomb {^ταλκ_{κοντριβς} – WP Physics} 01:50, 29 January 2009 (UTC)

Caesium iodide ;) Physchim62 (talk) 02:33, 29 January 2009 (UTC)

Thanks a bunch.Headbomb {^ταλκ_{κοντριβς} – WP Physics} 02:42, 29 January 2009 (UTC)

Lede style question

I edit a lot of chemical pages, kinda my hobby. But I want to follow the consensus about style. In general, I have been moving almost all of the "other names" for a compound into the ChemBox, except in cases where is a particularly widely used abbreviation. So in the case of acetone, I changed this:

"Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one, dimethylformaldehyde and β-ketopropane) is a colorless..."

into this:

"Acetone is the organic compound with the formula OC(CH₃)₂. This colorless ..." (with the other names in the chem box)

In some cases, a widely used acronymn or abbreviation is included in the opening sentence as in:

"Dimethyl sulfoxide (DMSO) is the chemical compound with the formula (CH₃)₂SO. It was first ..."

If other editors object to this approach or have suggestions, please let me know.--Smokefoot (talk) 19:05, 29 January 2009 (UTC)

"the formula OC(CH₃)₂." should be consistent with common organic compound indexing (as in any catalogue), so it would be better off as (CH₃)₂CO. Very minor issue, but it just doesnt look right. Endtothemeans (talk) 00:45, 31 January 2009 (UTC)

I agree that this is the best format. Having a long list of synonyms in the lede makes it unwieldy!

Ben (talk) 20:31, 29 January 2009 (UTC)

I think we should not have the formula in the intro, that's what the infobox is for. Cacycle (talk) 04:21, 30 January 2009 (UTC)

Whatever we decide, let's write it into the style guide. Til the next time consensus shifts. --Rifleman 82 (talk) 04:28, 30 January 2009 (UTC)

As a newbie, I was confused about this myself. I agree that only the most common synonyms should be in the lede; the rest are better placed in the infobox. Xasodfuih (talk) 04:42, 30 January 2009 (UTC)

I also concur that most--and in many cases, all--synonyms are better off in the infobox only. Yilloslime (t) 05:02, 30 January 2009 (UTC)

I often move uncommon synonyms, IUPAC names, and (sometimes) molecular formulas into the chembox, too. Definitely should be written into the style guide as Rifleman suggests. -- Ed (Edgar181) 13:34, 30 January 2009 (UTC)

I revised Wikipedia:WikiProject Chemicals/Style guidelines incorporating the advice given above but much more. Editors should take a look because I made several changes. For example:

• in the Preparation section, the methods should be presented in the order of the scale used, industrial routes get priority over lab methods. Cyclohexanone is generated on a massive scale by aerobic oxidation of cyclohexane, so the industrial method gets priority in sequence and in coverage over the chromate oxidation of cyclohexanol, which is done is schools.
• in the Applications section, I similarly recommend that "The order or presentation and allocation of content should ideally reflect the scale of the individual applications." For example, acetone article previously emphasized its handy solvent properties, but most of the 3 billion kiligrams produced annually is used to make some mega-products that the readership should be aware of. The recurring challenge (and balancing act) in the applications sections is that lay editors report domestic uses or mini-lab app's. The articles tend toward becoming self-help columns.

In any case, this Manual of Style is a consensus driven project and my comments are merely suggestions. --Smokefoot (talk) 14:32, 30 January 2009 (UTC)

Agree with Smokefoot on scale, and satisfied with changes to styleguide. However, some discretion should be applied with regard to routes - if we are talking about a biomolecule, obviously the biosynthesis should take precedence; on the other hand, for a molecule which is not primarily a biomolecule (e.g. acetone), the biosynthesis section should be last. Whichever the case, lab and industrial syntheses should not be separated by biosynthesis because the first two are "chemical" methods, and are thus linked, compared with the "biosynthesis" part. --Rifleman 82 (talk) 16:39, 30 January 2009 (UTC)

One more question. Bond lengths are often quoted in angstroms... are you proposing that we standardize to picometers (and that might not be a bad thing...)? --Rifleman 82 (talk) 16:54, 30 January 2009 (UTC)

Cgk733

I have nominated the chemical article Cgk733 for deletion. Please feel free to contribute to the discussion at Wikipedia:Articles for deletion/Cgk733. -- Ed (Edgar181) 13:36, 30 January 2009 (UTC)

Geometry of dichloro(cycloocta-1,5-diene)platinum(II)

Hi guys, quick question. Is this compound square planar, or tetrahedral? Pt is usually square planar, but I understand there are exceptions. Thanks. --Rifleman 82 (talk) 05:33, 4 February 2009 (UTC)

Inorg. Chem., 1984, 23 (22), pp 3673–3674 discusses the structure -haven't had time to read it thoroughly.

Ben (talk) 08:19, 4 February 2009 (UTC)

Thanks for your help, Ben! Care to draw the 3-D when you have a bit of time? :)

From the article, both double bonds are symmetrically coordinated. Based on the Cl-Pt-Cl bond angle, the molecule is square planar. The cod moiety is twisted though, giving the molecule an overal Cs point group. --Rifleman 82 (talk) 09:21, 4 February 2009 (UTC)

Yeah, it's usually considered to be square-planar. Physchim62 (talk) 09:47, 4 February 2009 (UTC)

I'd be delighted to draw the complex in 3D - I'll make a pic and upload it ASAP.

Ben (talk) 23:27, 4 February 2009 (UTC)

Pics now available at Commons:Category:Dichloro(cycloocta-1,5-diene)platinum(II).

Ben (talk) 00:50, 5 February 2009 (UTC)

Thanks Smokefoot & Ben! --Rifleman 82 (talk) 13:23, 5 February 2009 (UTC)

Octahedral carbon

I remember seeing a pretty graphical abstract with a crystal structure of a weird compound: a central carbon atom capped with six gold ligands. Anybody can remember a reference? I'm thinking it would be interesting to mention at Gold#Compounds. --Rifleman 82 (talk) 19:39, 4 February 2009 (UTC)

• doi:10.1002/anie.198815441 V8rik (talk) 20:38, 4 February 2009 (UTC)

• • Thanks, V8rik! --Rifleman 82 (talk) 13:22, 5 February 2009 (UTC)

Sodium naphthalenide and sodium cyclopentadienide

I can't seem to find any mention of a crystal structure of sodium naphthalenide and sodium cyclopentadienide. Are the structures I drew representative? Or can they be depicted better? Thanks! --Rifleman 82 (talk) 13:22, 5 February 2009 (UTC)

• I'm fine with your structure for CpNa, but not for sodium naphthalenide… in fact, I don't even agree with the formula you give! It's a radical cation, formed by electron transfer not deprotonation, and the extra electron is delocalised over both rings. Add to that the fact that it is almost certainly distorted by the Jahn–Teller effect. Suggestions anyone? Physchim62 (talk) 13:59, 5 February 2009 (UTC)
  • Thanks for that. I've taken it off the articleand put it here for discussion. --Rifleman 82 (talk) 14:17, 5 February 2009 (UTC)
• I've fixed the formula as well ;) Physchim62 (talk) 14:25, 5 February 2009 (UTC)

That's great, thanks. I saw that you insisted on the Na⁺Cp^- notation, but it wasn't consistently applied. I'm not sure if you're trying to emphasize some sort of ionic character, so I'll leave it to you. There remains a misplaced minus charge on the equations at the bottom though. --Rifleman 82 (talk) 14:27, 5 February 2009 (UTC)

Although it is nice to be consultative, checking the literature is the way to resolve these questions. The two species under question probably do not feature separated ions. Elschenbroich (Elschenbroich, C. ”Organometallics” (2006) Wiley-VCH: Weinheim. ISBN 978-3-29390-6) and Brandsma's organometallic manual probably deal with these issues. In the absence of a literature check, which could take some time, you could leave a short note on the Talk pages proding future editors to consider these questions. It is great that you identified these two issue, there are probably others. --Smokefoot (talk) 14:39, 5 February 2009 (UTC)

Thanks for your helpful comment. A quick check of the article (at least for NaCp) would have shown that it has several references to the secondary literature. As I'm sure you're well aware (and equally sure that Elschenbroich will confirm; what happened to Salzer btw?), the nature of the beast in a commercial THF solution is unlikely to be the same as that in a single crystal of the "pure" compound. Both are interesting for the article, of course, but the construction of our encyclopedia is both progressive and based on co-operation. Not everyone can do everything equally well, as Adam Smith famously pointed out. Physchim62 (talk) 16:52, 5 February 2009 (UTC)

I've found a crystal structure for NaCp: Organometallics, 1997, 16 (17), pp 3855–3858.

I can make a pic if it would add to the article.

Ben (talk) 15:49, 5 February 2009 (UTC)

Yes, please! I don't have scifinder access, and very limited journal access, so I'm sorry I keep coming here with literature questions. Thanks again, Ben! --Rifleman 82 (talk)

Xe

There is a suggestion to move Blackwater Worldwide to Xe and moving that page to Xe (disambiguation) 76.66.196.229 (talk) 05:20, 14 February 2009 (UTC)

Pinoline

Hi. I just started this page, tho I don't really know what I'm talking about. I took the info from just 1 apparently respectable source, but since the book is about free radicals, it may be one-sided. I've also seen suggested that pinoline has antidepressive effects, but those refs seem to be from the 90s - I'd rather see something newer.

The article needs control, infobox, and development from stub to article. Maybe also categories? Thanks, - Hordaland (talk) 18:24, 14 February 2009 (UTC)

Thanks for rapid attention, infobox, etc.! - Hordaland (talk) 23:53, 14 February 2009 (UTC)

No problem. It still needs some work. I but in three references as hidden comments so you might have a look.--Stone (talk) 08:00, 15 February 2009 (UTC)

Categorization of pharmacology articles

I started WP:PHARM:CAT in hopes of providing better guidance regarding the categorization of pharmacology articles. If available, I have posted an updated draft at WT:PHARM:CAT, and would appreciate your feedback. kilbad (talk) 23:16, 18 February 2009 (UTC)

Article alerts

I strikes me that it might be more useful to have the Article alerts on this page rather than on the project main page, so I've done an experiment. What do people think? Does it cause problems? Is it a useless waste of time here? I know I can trust you all to provide feedback! ;) Physchim62 (talk) 11:05, 19 February 2009 (UTC)

Great idea, unless there are too many alerts. My guess is that the editing community wants to be notified about new articles.If there are too many alerts then people will be turned off. Proposed moves and nominations for various levels of wiki-fame and deletion are less interesting, to me at least. --Smokefoot (talk) 18:09, 19 February 2009 (UTC)

I like it here, myself, but don't feel too strongly on it. I had no idea that ZnO was up for GAN! Walkerma (talk) 18:37, 19 February 2009 (UTC)

A quick note, if you don't like the DYK and stuff like that, you can turn theses of if you so wish. This is all detailed at WP:AAlerts#Subscribing and WP:Article alerts/Subscribing.Headbomb {^ταλκ_{κοντριβς} – WP Physics} 18:56, 19 February 2009 (UTC)

I don't really find it useful, since it is transcluded, and I don't notice updates. Is there an RSS feed or page which is updated, such that we can follow it on our watchlists? --Rifleman 82 (talk) 20:42, 19 February 2009 (UTC)

Well you can watch the page that is being transcluded (although you need to show bot diffs).Headbomb {^ταλκ_{κοντριβς} – WP Physics} 20:47, 19 February 2009 (UTC)

I can't parse the template.... would you mind giving us the page to display? From there, we can subscribe to RSS feeds if bot diffs are disabled. Thanks! --Rifleman 82 (talk) 20:55, 19 February 2009 (UTC)

Wikipedia:WikiProject Chemicals/Article alerts. Headbomb {^ταλκ_{κοντριβς} – WP Physics} 20:59, 19 February 2009 (UTC)

(redent) At present, we have the alert thingy set on a fairly long fuse (90 days): if the box gets too long, we can always change that in the last section of WP:CHEMS (which is where the instructions to the bot are kept). The idea of putting it here was that many people don't actually look at the project main page… I know I don't! We can also knock out some of the "claims to WikiFame" if that is so desired, but do remember that we only have one feed for all the project: unless Headbomb corrects me, we can't personalise it for each member. Physchim62 (talk) 23:00, 19 February 2009 (UTC)

Well there is a way of personalizing the reports on an individual basis, but it's rather convoluted. It involves setting up reports for each individual workflows (at pages such as /Deletion, /Good, /Feature, /DYK, etc.. Then users could transclude which workflow they want to see on a personnal page. But that's going pretty far to accommodate individual users for what is a minor inconvenience at worse. It's not like the bot updates individual items on the page, there's one update a day (when there is something to be updated). But if are willing to set this sort of thing up, then its definitely possible to do so. The details can be found at WP:AAlerts#Subscribing.Headbomb {^ταλκ_{κοντριβς} – WP Physics} 00:32, 20 February 2009 (UTC)

Sorry for the confusion, I didn't mean to ask for personalization. Wikipedia:WikiProject Chemicals/Article alerts works perfectly fine for me. Thanks. I watch the page history by RSS, and it's very usable. --Rifleman 82 (talk) 05:17, 20 February 2009 (UTC)

This is a good idea! I recently suggested that people keep an eye on FANs and GANs on WT:MED since somehow embarrassing articles got through last year because unlike FARs initial nominations don't have to be advertised to wikiprojects. (and no signifficant discussion + no opposes = FA by default it seems). I'm going to suggest that WP:MED use this alert system as well. Xasodfuih (talk) 08:09, 20 February 2009 (UTC)

Good idea to put the Alerts here. I do often look at the current statistics, so would it a good idea to put the Alerts a little bit higher on the page, somewhere in that same section? I'll give it a shot to indicate what I mean. Wim van Dorst (talk) 20:30, 20 February 2009 (UTC).

Member navbox

Also as a sidenote, I've made a {{Physics Member Navbox}} for physics members to put on their user pages (it basically is a repertoire of the various usefull links found in WP:PHYS). Maybe the members of this project would find it useful to have a similar template for them.Headbomb {^ταλκ_{κοντριβς} – WP Physics} 00:37, 20 February 2009 (UTC)

Notification of Science FAC symposium

• See Wikipedia:WikiProject Featured articles/Science FAC symposium. Ling.Nut ^{(talk—WP:3IAR)} 13:24, 20 February 2009 (UTC)

M(III) octahedral acac-complexes

I have an editor who wants us to give the "usual" synthesis of Fe(acac)₃ and similar β-diketonate complexes. He/She cites the references Bull. Chem. Soc. Jpn 1970 (43) 774-778; Inorg. Chem. 1963 (2) 411-412 to which I don't have immediate (or even simple) access. From memory, the prep is

1. dissolve the salt in water and add as much ethanol as is compatible with keeping it in solution
2. add the stoichiometric amount of Hacac
3. with good stirring, add a [stoichiometric+10%] quantity of a saturated solution of sodium carbonate dropwise to the mixture
4. extract or precipitate, dry, recrystallise

I'd rather have that confirmed before it goes on the encyclopedia though! Physchim62 (talk) 12:43, 24 February 2009 (UTC)

The second paper is here:

• M. L. Morris, R. W. Moshier, R. E. Sievers, "Infrared Spectra of Metal Chelate Compounds of Hexafluoroacetylacetone", Inorg. Chem. (1963) 2 (2), 411-412

I'll have a look on SciFinder for other papers later.

Ben (talk) 13:58, 24 February 2009 (UTC)

I think that many these preps are in Inorganic Syntheses and some in Organic Syntheses as well. Not sure that there is a general procedure for tris-acac's since the precursors vary widely. A lot of editors with affection with certain compounds (me included) sometimes forget and tend describe procedural details, but WE-MOS recommends against WE becoming a "user manual." So the procedural details like "good stirring", "dropwise", "dry in air" etc are usually inappropriate. --Smokefoot (talk) 14:26, 24 February 2009 (UTC)

Absolutely agree. Wikipedia is not a cookbook, and certainly not for chemical preps. I added the above just for illustration, not as an example of the details that we should include in an article. Even if we were to include all those details, we would still have to explain why it were necessary to add ethanol, whay it were necessary to have a 10% excess of sodium carbonate solution etc etc etc, and a thousand other variables that can only be taught in lab classes or by bitter experimental failure! Physchim62 (talk) 14:35, 24 February 2009 (UTC)

Article assessment

There are currently moves afoot to try to revitalise A-class assessments across Wikipedia (see here and here). What this means in practice is that we shall have to check that our twelve A-class articles still meet our criteria: if we don't do it, somebody else will! We have already had an outside editor come along and downgrade the assessment on sulfuric acid, quite justifiably in my view given the poor referencing of that article.

As we appear to have no choice in the matter, we might as well try glean as much benefit as possible from the process. The focus should be on article improvement, not simply an "A-class cull"! I also think we should take the forced opportunity of having to concentrate a little more on assessment issues to review our 393 B-class articles to see which could be promoted to A-class with a relatively small amount of effort. It might be useful to combine this effort with WP:CHEMISTRY (6 A-class, 24 GA-class and 282 B-class) given the near-complete overlap of editors between the two projects. Comments? Physchim62 (talk) 12:57, 26 February 2009 (UTC)

I'm happy to help from Sunday onwards. When should we start? Is Wim willing to participate, over at Wikipedia:WikiProject_Chemicals/List_of_A-Class_articles? Is there some way for us divvy up the B-Class ones? Let us know what you want us to do, PC. Thanks, Walkerma (talk) 04:17, 28 February 2009 (UTC)

WP:CHEM/ACR is close to being ready to go live, just needs a bit of polishing. WP:CHEM/BCR will take a little more time. Physchim62 (talk) 15:28, 28 February 2009 (UTC)

The trend to go after FA and A class articles is not always pleasant but very often very apt. Our best articles were of the highest quality in those early year (2005 is a long way back). Nowadays, WP has significantly higher standards regarding referencing, Fair Use, and copy-editing. So, this is a good trend. And I concur with PC that we better take our own plan here instead of waiting. After all, that's what we have always done: after all, who brought the assessment scheme to WP? The major problem with all this effort is that it focuses on the assessment scheme, procedures and standards, viz., the easy things. The hard things is in the article improvement effort: trying to find better and more information, finding appropriate references, and copy-editing the texts. So that awaits us all, what with busy jobs and other interests as well! Challenging, but a good thing. I'll am in, anyhow.

In the analoque quality effort, I've been plodding to get those last 2000 unassessed articles at least assessed. I'm making way very slowly, as new articles keep coming in nearly as fast as I can assess them. For the WP:CHEMS project progress I've reassessed the 382 articles of the worklist several times, but in all those hundreds of articles, I don't see easy wins. Best IMHO is simply to dig in on the A-Class ones, and make improvements where we deem necessary. I'll look at the ACR and BCR pages of PC, to see how they'll help. If my A-Class List should be re-vamped, just holler. Wim van Dorst (talk) 21:33, 28 February 2009 (UTC).

OK, we're up and ready to roll at WP:CHEM/ACR! The "article milestones" feature on the review pages doesn't fully work yet, but that is hardly essential. Come along and join in the "fun"! Physchim62 (talk) 20:33, 1 March 2009 (UTC)

Ammonium lactate

Should this substub be changed back to the redirect it was? --Leyo 16:36, 28 February 2009 (UTC)

• In my humble opinion it should be enhanced into a full FA-class article. Go ahead. I saw that Rifleman already reverted the stub to the redirect, but if you replace the redirect again with a full blown article, I'm sure he won't mind you trying again. Wim van Dorst (talk) 21:37, 28 February 2009 (UTC).

I didn't ask for the allowance to create an article. :-) --Leyo 02:11, 1 March 2009 (UTC)

Well, you don't need my permission in any case. We've discussed it some time back, that since there are really no limits to the number of compounds possible, less notable compounds should simply be redirected to the parent acid. I recall there weren't violent objections then. A google search of ammonium lactate shows lots of hawkers trying to sell some cream or ointment. Some of the information out there is simply crazy. "Ammonium lactate is a combination of lactic acid and ammonium hydroxide." from [6]. Anyway, if it can be written into a meaningful article, I'm all for it. --Rifleman 82 (talk) 04:42, 1 March 2009 (UTC)

Making our style guide official

We agreed on IRC that it's about time we ratified the use of our style guide. Please can everyone take a look at Wikipedia:Manual_of_Style_(chemistry)/draft and comment, discuss and edit, so we can get this fixed up ready for use? We will also discuss this on IRC at channel #wikichem on freenode on Tuesday, March 3rd at 1600h UTC (11am US ET, 1700h CET), all are welcome. Thanks, Walkerma (talk) 02:44, 28 February 2009 (UTC)

I'm teaching until 1700 UTC (1800 CET), as last week, but I've leave IRC open and logging to catch the discussion. Physchim62 (talk) 11:37, 28 February 2009 (UTC)

The MOS is semi-important because it is the rule book guiding content. A good place to make comments is probably at the talk page. Some controversial topics:

• safety sections that get inflated with anecdotes, advice, and content obtained by Googling.
• referencing - many editors feel the tension between citing primary sources and Wikipedia's official preference for more "digested" secondary sources. Many people fail to appreciate that a primary cite often means little - scientists and journals are paid to publish. On the other hand we like to credit discoveries with the primary citation.
• trivia - what is trivial and what is valid content? Should be enumerate chemical accidents reported in the news, mention niche domestic app's (it makes a great paint stripper ..),
• Advice and advocacy - some articles lean toward offering advice or condemning this or that compound.

Again these and other themes can be further discussed at our MOS talk page.--Smokefoot (talk) 15:54, 28 February 2009 (UTC)

Hexan-2-one

Hello! I am a article reviewer at articles for creation and recently had this article submitted for review. I created the article, but am not clear on the appropriate nomenclature. Should this article exist at 2-butanone? Should it redirect/be merged to Butanones? Any assistance is appreciated. Best, TNXMan 19:27, 3 March 2009 (UTC)

This article should not be moved to 2-butanone or butanones because it's a hexanone (six carbons, not four as for butanones).

The current article title is in IUPAC and UK-style, but the American-style "2-butanone" is more common (Google, "hexan-2-one" 11200; "2-hexanone" 43700).

Ben (talk) 21:31, 3 March 2009 (UTC)

Ah, thank you. The reason I asked was the article said it was commonly known as 2-butanone. Does that need to be changed then? Thanks for the assistance! TNXMan 21:42, 3 March 2009 (UTC)

The article title is fine according to WP:NCCHEM. 2-Hexanone would also be acceptable, but I've made it into a redirect instead. I will check and grade the article. Physchim62 (talk) 21:53, 3 March 2009 (UTC)

Element vs ion

Is there some guideline as to what should go into the article on the ion vs the article on the element? I'm trying to figure out if fluorine and fluoride have the appropriate contents; the look more or less like a WP:CFORK to me right now. Xasodfuih (talk) 17:32, 4 March 2009 (UTC)

Ah yes! Those guidelines! The ones about anion-specific articles that I said I would write about, what, three years ago now, and never got round to it!

To quickly answer the case in question, you're right, there's a lot of material in Fluoride that should really be there. That article should concentrate on inorganic fluorides to fit in with the General Scheme of Things (under construction). We have organofluorine chemistry to act as an introduction to this large field of chemistry. The fluorine article can only hope to be a brief summary of the unique chemistry of this element, and so, apart from the necessary examples, should concentrate on why the chemistry is unique and on the points which allow chemists to draw some sort of coherence to the chemistry of fluorine. Physchim62 (talk) 18:11, 4 March 2009 (UTC)

And where would you put the discussion of fluoride as micronutrient (and also its toxicity)? I'm guessing in fluoride because you'd normally ingest it as a (dissolved, but inorganic) salt. Xasodfuih (talk) 19:22, 4 March 2009 (UTC)

Yes, those aspects should really go in fluoride, probably in summary style given the range of such topics (water fluoridation, fluoride contamination from aluminium smelters, fluorosis, etc), not to mention the simple chemistry of the salts (why are they often high boiling point but not always, why are they often fairly insoluble in water, etc). Physchim62 (talk) 22:22, 4 March 2009 (UTC)

Anethole

Does this:

Carteau D, Brunerie P, Guillemat B, Bassani DM (2007). "Photochemistry in everyday life: the effect of spontaneous emulsification on the photochemistry of trans-anethole". Photochem. Photobiol. Sci. 6 (4): 423–30. doi:10.1039/b614244c. PMID 17404637. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

say that microemulsions of trans-anethole are more stable than "homogeneous" solutions? What are these homogeneous solutions? I'd like to work this into the articles Anethole and Ouzo effect. --Una Smith (talk) 04:31, 8 March 2009 (UTC)

I got a copy of the article, thanks! --Una Smith (talk) 02:31, 10 March 2009 (UTC)

Next question: what is (E)-anethole? More generally, what does (E)- connote? --Una Smith (talk) 02:31, 10 March 2009 (UTC)

E - entgegen (opposing); Z - zusammen (together). Referring to the position of substituents on the alkene double bond at left. Something like cis-trans. --Rifleman 82 (talk) 05:54, 10 March 2009 (UTC)

Danke! --Una Smith (talk) 06:03, 10 March 2009 (UTC)

(E)-Anethole is the same as trans-anethole: (Z)-anethole is the same as cis-anethole. The (E/Z)-nomenclature becomes important when you have three or four groups attached to the double bond, rather than just two as in anethole, but many authors use it when there are just two groups as well. Physchim62 (talk) 15:02, 11 March 2009 (UTC)

Got it. E-Z notation explains this, but not that E- and (E)- are the same. The added parentheses led me to wonder if there was some extra/other meaning. Could you all expand on that in the article, for non-chemists? --Una Smith (talk) 03:50, 13 March 2009 (UTC)

Thanks for pointing that out. The article wasn't actually wrong, but was pretty badly written. I've tried to improve it a little, but it needs some more work. Physchim62 (talk) 15:28, 13 March 2009 (UTC)

Yes, it was in there, just not clear. Now it is much clearer. Thanks! --Una Smith (talk) 16:52, 13 March 2009 (UTC)

Deletion of wrong or poor structures

There is an ongoing discussion on the Commons about the deletion process for tagged wrong or poor structures. Your input would be welcome on Commons:Administrators' noticeboard#Superseding. Cacycle (talk) 14:14, 13 March 2009 (UTC)

Article alerts

This is a notice to let you know about Article alerts, a fully-automated subscription-based news delivery system designed to notify WikiProjects and Taskforces when articles are entering Articles for deletion, Requests for comment, Peer review and other workflows (full list). The reports are updated on a daily basis, and provide brief summaries of what happened, with relevant links to discussion or results when possible. A certain degree of customization is available; WikiProjects and Taskforces can choose which workflows to include, have individual reports generated for each workflow, have deletion discussion transcluded on the reports, and so on. An example of a customized report can be found here.

If you are already subscribed to Article Alerts, it is now easier to report bugs and request new features. We are also in the process of implementing a "news system", which would let projects know about ongoing discussions on a wikipedia-wide level, and other things of interest. The developers also note that some subscribing WikiProjects and Taskforces use the display=none parameter, but forget to give a link to their alert page. Your alert page should be located at "Wikipedia:PROJECT-OR-TASKFORCE-HOMEPAGE/Article alerts". Questions and feedback should be left at Wikipedia talk:Article alerts.

Message sent by User:Addbot to all active wiki projects per request, Comments on the message and bot are welcome here.

Thanks. — Headbomb {^ταλκ_{κοντριβς} – WP Physics} 08:56, 15 March, 2009 (UTC)

Cyclopentasiloxane

The article name, the CAS RN and the structure do not match. --129.132.224.86 (talk) 13:11, 17 March 2009 (UTC)

It's the structure that's wrong: there's now way that the pentamethyl compound would be used for the applications mentioned, it would be far too reactive. The CASRN and the MSDS refer to decamethylcyclopentasiloxane: I have no refs, but I can quite believe that "cyclopentasiloxane" is used as a trade synonym for this compound. Physchim62 (talk) 13:20, 17 March 2009 (UTC)

What about moving the article to decamethylcyclopentasiloxane (similar to the article on de-WP)? --Leyo 14:31, 17 March 2009 (UTC)

Requested move

It is my opinion that the current names of the articles and categories

• List of IARC Group 1 carcinogens, Category:IARC Group 1 carcinogens
• List of IARC Group 2A carcinogens, Category:IARC Group 2A carcinogens
• List of IARC Group 2B carcinogens, Category:IARC Group 2B carcinogens
• List of IARC Group 3 carcinogens, Category:IARC Group 3 carcinogens
• List of IARC Group 4 carcinogens, Category:IARC Group 4 carcinogens

are misleading, since all agents (materials, compounds, environments) could and should be classified by IARC. The classification does not make them "carcinogens".

Please comment at Talk:International Agency for Research on Cancer#Proposal to move several articles/categories to alternative names.--FocalPoint (talk) 20:12, 20 March 2009 (UTC)

Category:Compound images

IMHO this category and some of the contained images should be deleted. --Leyo 20:56, 1 April 2009 (UTC)

Agree, the category should go. ALL such images should be on Commons. As for the images to be deleted (rather than transferred to commons), File:Acetone peroxide molecule.jpg is an obvious case: I would tend to say that we redraw anything which isn't PNG or SVG and then delete the current files as superfluous, otherwise we transfer to commons. Opinions? Physchim62 (talk) 22:11, 1 April 2009 (UTC)

I count half of this category (8/15) as JPGs. I'll start looking to see if we already have alternatives. shoy (reactions) 01:11, 2 April 2009 (UTC)

Unused

• File:4Bromo1anisolea.svg

Superceded

• File:Acetaminophen.png

Unused, Superceded Anyways

• File:Acetone peroxide molecule.jpg
• File:Adenosine.png
• File:Fumonisin B2.JPG
• File:Glyceraldehyde3-phosphate.png
• File:Glycerol-Structure.png
• File:Isomigrastatin.JPG
• File:Migrastatin.JPG
• File:Periplanone B.JPG
• File:Simvastatin.JPG
• File:TAN-1057 A.JPG
• File:TAN-1057 C.JPG

Used

• File:Methyl Violet 2B.png - used in Methyl violet, is on commons
• File:Triglyceride-GeneralStructure.png - used in Triglyceride, Oil, Lipase, probably needs to be redrawn

shoy (reactions) 01:23, 2 April 2009 (UTC)

There is alternative for the last one: File:Triacylglycerin.svg.

File:Adenosine.png should be deleted along with the JPG files as there is a better alternative on Commons with the same name (i.e. currently prevented from being used). --Leyo 06:44, 2 April 2009 (UTC)

The following images could should be able to be speedy deleted under I8 since they are identical but only displayed differently due to standards used but they were all denied because they weren't "identical" so someone will have to open up a mass IFD discussion for it:

• Local Copy => Commons Version
• File:Fumonisin B2.JPG => File:Fumonisin B2.png
• File:Glyceraldehyde3-phosphate.png => File:G3P-2D-skeletal.png
• File:Glycerol-Structure.png => File:Glycerin Skelett.svg
• File:TAN-1057 A.JPG -> File:TAN-1057A.png
• TAN-1057 C.JPG => File:TAN-1057C.png
• File:Methyl Violet 2B.png => Same Name

There are some more compounds listed at Wikipedia_talk:WikiProject_Chemistry#Chemical "layout" drawings that could be duplicates and need sorting/tagging/deleted/transferring ect. Peachey88 ^{(Talk Page · Contribs)} 09:37, 12 April 2009 (UTC)

GA Class

This projects needs an article category for GA Class articles, Alprazolam was rated GA class but the rating can't be displayed for the Wikiproject on the talk page. Hekerui (talk) 12:29, 3 April 2009 (UTC)

This project doesn't use GA-class, and never has done. The fact that Alprazolam is a Good Article is already displayed on the article talk page. Physchim62 (talk) 13:52, 3 April 2009 (UTC)

So what do you think the Project rating should be? Hekerui (talk) 17:27, 3 April 2009 (UTC)

Well, B-class is the highest rating that a single editor can give in this project, so that's what I've given it for the time being. I actually wonder why it is tagged as a WP:CHEMS article: there doesn't seem to be a great deal of chemical interest in the compound (as opposed to the obvious pharmacological interest). For a chemist, it's just another benzodiazepine! I'll let others comment before removing the project tag. Physchim62 (talk) 18:02, 3 April 2009 (UTC)

The article is about a chemical compound, so I would accept it within the Chemicals wikiproject, in line with the other 5000 chemical compound articles. The rating of the article in the project is a (meagre) B-Class: there is limited chemical info, no chembox, etc, so for A-Class much development would be required. And as pointed out, there is no GA-class in WP:CHEMS, for historic reasons. Wim van Dorst (talk) 21:50, 3 April 2009 (UTC).

Article request

Will someone create an article stub on zirconium lactate? I created a link at zirconium granuloma. kilbad (talk) 18:04, 7 April 2009 (UTC)

 Done Could you check my description of the dermatology? Physchim62 (talk) 20:07, 7 April 2009 (UTC)

Looks great... thank you so much for your quick reply! kilbad (talk) 20:10, 7 April 2009 (UTC)

NaPH₂

What would you call this compound? Sodium phosphanide? Monosodium phosphide?

Its CAS number is 24167-76-8, and I guess it's similar to sodium amide, NaNH₂.

Ben (talk) 15:47, 11 April 2009 (UTC)

Sodium phosphanide would be the IUPAC name, and probably best to avoid confusion. Physchim62 (talk) 18:01, 11 April 2009 (UTC)

Nice one, ta.

Ben (talk) 22:13, 11 April 2009 (UTC)

Better 3D Structure Displays for Wikipedia

Many Wikipedia pages on chemicals now have statically rendered PNG images of 3D structure models. Nice to look at, but not too useful in practice.

We have developed technologies to generate PDF files with interactive 3D chemical structure models (see http://85.214.71.72/pdf3d for an interactive demo with the PubChem structures) from essentially any chemical structure data source with 3D coordinates, or at least amenable to computing these (for example, via chembiogrid.org). These files can be viewed on any system with Acrobat Reader 7 or later - meaning this is a much more reliable, convenient and portable approach than using Java viewers, VRML/X3D plug-ins etc.

We are willing to donate such PDF image files to Wikipedia under the creative commons license (i.e. for now, feel free to use above link to download and integrate these files for the entries with PubChem references).

Is this something the community is interested in picking up? And a more fundamental question: Can Wikipedia use embedded or linked PDF files for annotations?

KommanderalKashenblade (talk) 14:29, 12 April 2009 (UTC)

That's very interesting, and nice models indeed! Can you comment further on why you think that using Adobe Reader has benefits over using Java? --AngelHerraez (talk) 19:45, 12 June 2009 (UTC)

Well, the main advantage is that Adobe reader is already installed about anywhere. Java is not, and there are many potential scenarios where users may not be able to install additional software. Also, start-up is quicker than Java - there is no viewer app data download.

Element names in templates

It would be nice if section 1.3 (Element names) includes a remark about not allowing "incorrect" spelling anywhere, including in templates where their names are not normally visible to the reader. User:Hgrosser has been modifying many of the physics templates I created to allow incorrect spellings. I've undone these changes and pointed him to this article, but he has continued to modify templates. I assume that an explicit message in the style guide will deter him from modifying any more templates. (As a side note, from his talk page, it seems that he has a tendency to be a bit blunt in his spelling changes)

    — SkyLined { talkcontribs 16:38, 15 April 2009 (UTC)

New cleanup template: {{Chemformula}}

Which can be used in sentences like:

Iron nitride{{chemformula}} may be super awesome, but buckminsterfullerenes{{chemformula}} are clearly even more awesome.

It populates Category:Articles needing chemical formulas. Feel free to tweak the text, and categories, etc... Headbomb {^ταλκ_{κοντριβς} – WP Physics} 21:56, 16 April 2009 (UTC)

I could do a similar thing as I did for Category:Nuclide templates: create a switch with known compounds which outputs the right chemical formula (if it's in the switch) or the superscript text it shows now if it's unknown. That would mean you only have to add the formula once to the template and everybody that used the template will instantly benefit from having the formula inserted. eg [[Iron nitride]]{{Chemformula|Iron nitride}} would output the request to add the formula until it's added to the template, after which it will output the formula in all pages that use it.

    — SkyLined { talkcontribs 22:22, 16 April 2009 (UTC)

The problem is that there are way too many chemicals to even attempt to make a template like that.Headbomb {^ταλκ_{κοντριβς} – WP Physics} 23:08, 16 April 2009 (UTC)

Main discussion at Wikipedia_talk:WikiProject_Chemistry#New_cleanup_template:_.7B.7BChemformula.7D.7D. --Rifleman 82 (talk) 04:44, 17 April 2009 (UTC)

Benzopyrene

What would people think about moving this page to something like Benzo(a)pyrene and converting Benzopyrene into a general page about the different benzopyrenes? (Brackets aren't allowed in page names due to technical restrictions, which is why the page can't be at Benzo[a]pyrene.) shoy (reactions) 16:46, 22 April 2009 (UTC)

Is there a WP article describing the function of the square brackets in chemical names like this? – Would be good in the 'See also' section or other appropriate place in articles with such names. --83.253.240.46 (talk) 19:05, 22 April 2009 (UTC)

If you want to expand IUPAC nomenclature of organic chemistry to summarize all the hundreds of pages of constantly-updated naming rules, be my guest. shoy (reactions) 00:16, 23 April 2009 (UTC)

I support Shoy's proposal of general and then subpages on the benzopyrenes. Although not always driven by the technical problems associated with typography, we have created many master and then specialized articles, e.g. with bipyridine and then 2,2'-bipyridine. (Is there a list of "forbidden" typography? We periodically have problems with the various kinds of apostrophes in article names).--Smokefoot (talk) 23:07, 22 April 2009 (UTC)

"forbidden typography"? --83.253.240.46 (talk) 23:34, 22 April 2009 (UTC)

I should note that the article has been moved to Benzo(a)pyrene, so if someone wants to help me create an article on benzopyrenes in general, I would be appreciative. shoy (reactions) 01:44, 23 April 2009 (UTC)

Bromonium ion

Is the structure in that article correct? Shouldn't it be BrH2+? --83.173.237.152 (talk) 10:50, 26 April 2009 (UTC)

Fixed and ref'ed to Gold Book. Cacycle (talk) 19:30, 26 April 2009 (UTC)

Does this structure (dimethyl bromonium ion) that was removed from the article exist? If not, it might be deleted. If yes, a nicer version should be uploaded to Commons. --Leyo 10:24, 27 April 2009 (UTC)

I had a look on SciFinder. There are 14 refs, plus 1 or 2 on its AsF₆⁻ and SbF₆⁻ salts - no xtal structures, though:

• J. Phys. Chem. A (2008) 112, 11468–11480: "Topological Insights into the Nature of the Halogen−Carbon Bonds in Dimethylhalonium Ylides and Their Cations"
• J. Org. Chem. (2006) 71, 2625–2629: "Intrinsic Acidity of Dimethylhalonium Ions: Evidence for Hyperconjugation in Dimethylhalonium Ylides in the Gas Phase"
• J. Am. Chem. Soc. (1998) 120, 1538–1544: "An Experimental and Theoretical Investigation of Ion−Molecule Reactions Involving Methyl Halide Radical Cations with Methyl Halides"
• J. Chem. Soc., Perkin Trans. 2 (1991) 1187-1194: "Investigations of halonium ions in the gas phase"
• J. Am. Chem. Soc. (1969) 91, 2113-2115: "Friedel-Crafts chemistry. IV. Dialkylhalonium ions and their possible role in Friedel-Crafts reactions"

I've got the crystal structures of a few halonium ions in the pipeline, so I'll add them soon-ish.

Ben (talk) 22:18, 12 May 2009 (UTC)

Cleanup

See also: Wikipedia talk:Chemical infobox § Cleanup

I am spending some time on the {{chembox}}, and decided to pick up something that has been lying around for some time: there are boxes out there which have parameters in the main body of the box, which really should be in the 'sub-boxes' (e.g.:

{{Chembox|name=benzene|formula=C6H6}}

, where it should be

{{Chembox|name=benzene|Section1={{chembox properties|formula=C6H6}} }}

. Chembox does still support those vars, but I am now in the process to a) move the parameters into the appropriate subboxes, and then, when ready, removing that support. Some help would be appreciated. Chembox now categorises the 'wrong' articles in Category:Chemical infoboxes with misplaced or deprecated parameters (which should be empty after some time).

People may also be interested in the discussion above the above mentioned one, Wikipedia talk:Chemical infobox#Please insert SMILES into SMILES field, regarding thoughts about merging {{chembox}} and {{drugbox}} (this does NOT mean that we are ready to remove drugbox, but I'd like to explore some possibilities and ideas there). --Dirk Beetstra ^{T C} 10:04, 30 April 2009 (UTC)

Category:Chemical infoboxes with misplaced or deprecated parameters is empty, except for user subpages, because I just cleaned it up a couple days ago. :) (User:Shoy) 136.165.49.108 (talk) 15:13, 12 May 2009 (UTC)

Expert advice needed for gamma boron issue

Recently, the page Gamma boron discovery controversy has been created. It would be wonderful if some chemists could comment on the article's talk page whether this is actually an active controversy. In particular, no professionally published sources on the controversy have been found. — Carl (CBM · talk) 23:49, 12 May 2009 (UTC)

In the context what I understood, I do not see any priority problems. One group in 1965 discovered it but was not able to do a structural analysis, for me they discovered it, than the next group solved the structure and found that this is a new structure and got credited for the discovery of the new gamma boron in the last step the last grroup was able to do single crystal structure analysis giving a better insight into structure and properties like hardness and other things. The manuscript transfer from one group to another makes it impossible to find the truth what happened afterwards, if we do not have the spanish Inquisition at hand.--Stone (talk) 17:41, 13 May 2009 (UTC)

Non-primary sources - let's stick to that policy

The WE guidelines recommend against primary sources. The recent controversial business with gamma boron arose from the focus on primary sources. I have previously mentioned: J. Phys Chem alone last year published 45,000 pages. It is one of hundreds of chemical journals. It is very, very difficult to select recent work or we invite the following trouble:

• nasty battles like the gamma boron issue
• vanity citations
• self-styled experts highlighting "pet papers," a form of OR.

Editors should recommit to WP:SECONDARY sources and tertiary sources. To quote from this section of the manual "Wikipedia articles should rely mainly on published reliable secondary sources and, to a lesser extent, on tertiary sources." If editors disagree with this policy, let's talk about it here and incorporate our consensus-conclusions into our own manual of style.--Smokefoot (talk) 12:52, 13 May 2009 (UTC)

• Disagree: peer-reviewed articles such as those published in J.Phys.Chem ARE secondary sources, to quote from WP:SECONDARY  :

Primary sources are sources very close to an event. For example, an account of a traffic accident written
by a witness is a primary source of information about the accident. Other examples include archeological 
artifacts; photographs; historical documents such as diaries, census results, video or transcripts of
surveillance, public hearings, trials, or interviews; tabulated results of surveys or questionnaires;  
original philosophical works; religious scripture; published notes of laboratory and field experiments or 
observations written by the person(s) who conducted or observed the experiments; and artistic and fictional
works such as poems, scripts, screenplays, novels, motion pictures, videos, and television programs. The key
point about a primary source is that it offers an insider's view to an event, a period of history, a work of  
art, a political decision, and so on 

V8rik (talk) 17:24, 13 May 2009 (UTC)

Okay, then I respectfully recommend a revised policy that encourages tertiary sources - we just need to get away from the primary journals to the extent reasonable. Otherwise we will have continuing problems with turf-wars, vanity, and OR. The vanity-OR aspects get less attention but are more serious problems in my view because they distort without detection. The guideline is only that, we'd still need to cite some journal articles (I do it often too, but less than I used to). Problems with turf-vanity-OR would be fewer if reviews and overviews were our main feedstock. My suggestion (which is probably not very widely accepted) is also based on the fact that citations are only added, virtually never removed (or the deleting editor faces near-crucifiction). So WE is headed for congestion with the journal emphasis - our articles will end up with thousands of citations each. The novice trying to understand an area will be unable to distinguish time-tested references vs an individual journal articles, so we are doing a disservice to our readers (although none of us intend that).--Smokefoot (talk) 22:34, 13 May 2009 (UTC)

I've tried to give detailed (maybe too detailed) guidelines at WP:MOSCHEM/SAFE. Another model is the medics' guidelines at WP:MEDRS (generally accepted by the WP community within its field, as are most well-drafted scientific guidelines). I've often asked myself whether we should have a WP:CHEMRS, but I have always felt that it was too difficult to find a single set of guidelines which would satisfy everybody on this project over all the fields that we cover. Maybe now is the time to prove me wrong! Physchim62 (talk) 23:01, 13 May 2009 (UTC)

i think despite peer review and the fact most of a journal article is secondary, an article's novel findings are still a primary source per "observations written by the person(s) who conducted or observed the experiments" (quoted above); after all, while peer review smooths out text, it does not connote authorship. i share Smokefoot's concern over the misuse of primary sources, and i agree that the project could be strengthened greatly by more tertiary sources. however, an over-focus on tertiary sources does limit the ability to write an encylopedia. secondary sources are the heart of this project, and rightly so, in my opinion, as WP aims to be a tertiary source. furthermore, this project does officially encourage the creation of novel articles not found in traditional tertiary/encyclopediac sources. -Shootbamboo (talk) 00:14, 16 May 2009 (UTC)

It is perfectly OK for me to cite journal articles (primary sources) for notable new findings for which no review articles (secondary sources) have been published yet. For these cases it would be good to have a guideline / example formulation to indicate the preliminary and unverified state of such findings. Cacycle (talk) 00:59, 16 May 2009 (UTC)

Sheepishly: kind of sorry I brought the subject up, because I add journal refs all the time too. But I was alarmed by the semi-ridiculous Gamma boron discovery controversy. It would not hurt to add a few words into the Chem-MOS, knowing that lots of exceptions exist. (In my place, we call journals primary, reviews/monographs secondary, encyclopedia tertiary). Otherwise, maybe this topic would generate more anxiety than enlightenment among the editors.--Smokefoot (talk) 02:54, 16 May 2009 (UTC)

• WP:MOSCHEM/SAFE only has something to say about safety info , to quote again:

Editors are strongly discouraged from using the primary literature (eg journal articles) 
 as sources for chemical safety information.

the guidelines in WP:MEDRS have something to say about medical literature

Many, but not all, papers published in medical journals are primary sources.

This discussion pops up regularly but never comes to a conclusion, perhaps we need a clear ruling on the WP:SECONDARY page on this. My question to this group: how are we to attract chemists to wikipedia if we are only allowed to copy from reviews / other encyclopedias?. V8rik (talk) 21:42, 16 May 2009 (UTC)

I am interested in some clarity. As far as I can tell, I think this is the central question: does citing information from a journal article (that is cited from another journal article) constitute citing a primary or secondary source? My opinion is that it is a secondary source, as it is one step removed, despite the common designation of journal articles being primary sources. -Shootbamboo (talk) 22:06, 23 May 2009 (UTC)

The distinction betweeen primary and secondary sources versus original research articles and reviews has not been made clearly, and often confuses people who aren't logically precise. You are correct that an original research article is a secondary source for most of its facts (seen in the introduction and discussion sections). A review article is sometimes a more complete secondary source, particularly if the review is systematic (ie complete). Reviews often synthesize articles to come up with original conclusions (the total evidence says such and such), whereas original research articles are generally original in their main research. Reviews are, without a doubt, primary sources for their synthetic conclusions. Anyone who doens't properly accept or understand this distinction should not be taken seriously, and I'm glad that most of the commentators above seem to accept this.

There's some confusion about the "consensus" on MEDRS and how big of a deal MEDRS is. Yes, reviews should generally be used, but the consensus over MEDRS being promoted to a guideline and then used rather indiscriminately consisted of around 3-4 self-described MDs and a few more interested laypeople, whereas the opposition consisted of one self-described professional medical researcher (User:Paul gene) and a small handful of interested laypeople, if I recall correctly. I'm somewhere in the middle -- I didn't vote on the RfC, but I'm disturbed b the indiscriminate use of reviews which are clearly factually incorrect in light of the original research articles cited (or in some cases, complete lack of citations). See, for example, this discussion. The problem with loosely-researched secondary or tertiary sources was exemplified when we recently ran into this issue at zinc, where a chemistry professor was off by an order of magnitude on the amount of zinc left in the world, called fluoride an essential nutrient, and probably made errors on zinc's biological activity. The idea that tertiary sources are more reliable is, frankly, ludicrous, and we should avoid citing Britannica and the popular press whenever possible. II | (t - c) 05:50, 24 May 2009 (UTC)

WikiChem and CAS

This might not be news to many readers, and I apologise for the slight delay in bringing the information here. Several editors at WP:CHEMS have been working to verify the CAS Registry Numbers quoted in our chemboxes against a primary source, a file provided by CAS itself. This is a big task, and it's still not complete. The dataset from which we have been working has now been made public, so we can work towards a more open, wiki-based method of verification. This will all allow us to "cite our sources" in the normal Wikipedia way, something which has been impossible up until very recently when it comes to CASRNs.

It has taken us over a year to get to this point, and the discussions have not always been friendly (even within the "two sides", let alone between them). As ever with Wikipedia, there is still a lot to do! All the same, we now have another "anchor" to add to our InChI data (the two are complementary) to make sure that we get the right data for the right compound, and that our users can do so as well.

It would be petty to single out names of those who've helped; in any case, I have no position to do so. Instead, adapting a long-standing tradition of this project, I shall declare a general free beer.* Physchim62 (talk) 22:31, 13 May 2009 (UTC)

[* subject to the normal WP:CHEMS free-beer conditions, of course ;) ]

Everyone should probably pop over to Wikipedia:Wikipedia_Signpost/2009-05-18/Chemistry_data and read Physchim's excellent article about this, by the way. (User:Shoy, public terminal) 136.165.49.81 (talk) 19:03, 19 May 2009 (UTC)

Really good article - I didn't really understand all this talk of CheMoBot and verification until I read it.

Ben (talk) 19:40, 19 May 2009 (UTC)

I'm sorry the article wasn't created in a more wiki-like manner but, as the revision history shows, it really was whipped up in the small hours of Monday morning (CEST) with the Signpost deadline looming… There is also a more formal press release if anyone wants it. The initiative is creating a few waves in the chemical information community, judging from the blog/forum posts I've seen, let's hope we can keep it moving forward. Physchim62 (talk) 19:53, 19 May 2009 (UTC)

Merge request for copper sulfide, copper monosulfide and copper(I) sulfide

You might like to have a look at this request to merge the above three articles as this represents a far reaching precedent if it goes ahead. --Axiosaurus (talk) 11:50, 14 May 2009 (UTC)

Chemical template data

Hello everyone. As some of you may have noticed and may be concerned that I have been making many minor additions (with a few changes) to the infoboxes of (inorganic) compounds. First off, I want to add that I believe in the rights to free information and free knowledge. I noticed that the properties for the chemicals are so far lacking some readily available information. I have 3/4 good source books dating as recent as 2004 with this information in them. I'm trying to cross-reference this information as much as I can to find, for example, the "most accurate" melting point of a substance. All my edits have been in good faith, as accurate as I can find and to expand knowledge (which to me, is what Wikipedia is about). I just wanted to make the community aware of my intentions and hope to hear some suggestions. PS. Sorry for all the run-on and fragmented sentences - English was never my strong-point. Thricecube (talk) 01:27, 20 May 2009 (UTC)

The main thing I have seen is that you're adding information without sourcing it. shoy (reactions) 01:41, 20 May 2009 (UTC)

Fair enough. I'm not completely confident on how to source, but I will try to do a better job with it. Thricecube (talk) 01:47, 20 May 2009 (UTC)

First of all, a salute to Thricecube (assuming his data is decent...)! To what extent do we want citation associated with each datum in a ChemBox? Our Chem MOS does not seem to specify. That CoCl₂ is blue? Or melting points of xyz? A ref for each datum? Similarly, some solubilities are being given at more than one temp? How many temperatures are sufficient? I could go on... For example, some editors give an extended list of solvents (MeOH, EtOH, Me2CO, ...) for a given cmpd.--Smokefoot (talk) 02:24, 20 May 2009 (UTC)

I didn't even know that the | Reference = parameter in {{chembox}} existed until recently... maybe there's an opportunity to modify the template to make citing sources easier? Especially if you're using multiple sources in the chembox and you don't want to have to put a source in every single box! (User:Shoy, public terminal) 136.165.49.81 (talk) 15:31, 20 May 2009 (UTC)

I would favour having all the references in a given section (Identifiers, Properties, Hazards, etc. collected together at the top of that section, with a Reference parameter in each section. I stuck a Reference parameter in {{Chembox Identifiers}} when we changed it recently for the CAS data. Physchim62 (talk) 08:45, 21 May 2009 (UTC)

Good plan, Physchim62. The others can easily be adapted to that. I would say that for the majority of the data, general references are fine. For most of the 'older' and for the general compounds (solvents) the data can be referenced in the standard way, and I would encourage just a link to such a page in the bottom, with the 'standard conditions' link. For 'newer' compounds, some data simply is unknown. The data there that is known and does not come from the standard sources, should have specific references. The reference tag in the modules is certainly then a good place, it can contain more references than one (just put reference=<ref>ref 1</ref name=boilingpt><ref name=refractiveindex>ref 2</ref>. I would expect that it will generally stop at maximum of 2-3 sources anyway. --Dirk Beetstra ^{T C} 14:24, 21 May 2009 (UTC)

Exactly. I don't think we will ever really need more than about three references per section: if we need more, that probably means that we should be discussing a particular property in the article text and placing the references there. If we're going to implement this, can we simplify my appalling code in the chembox modules at the same time? ;) Like I did for {{Chembox Identifiers}}… I can recode them in local sandboxes (and test the results) if there is sufficient support. Physchim62 (talk) 15:16, 21 May 2009 (UTC)

This sounds like a good idea. shoy (reactions) 16:10, 21 May 2009 (UTC)

Wikipedia's coverage of chemicals in PubMed

I just ran a few scripts to compare Wikipedia's index to chemical names found in PubMed, see my blog post. I also created list of missing chemicals and missing synonyms (i.e. redirects), ordered by the number of hits in PubMed. MichaK (talk) 13:50, 21 May 2009 (UTC)

Interesting lists. Some of them are more pharmaceutical, I think, but certainly many are chemicals. And if they are in PubMed/PubChem, many may be notable enough for an own article. Thanks! --Dirk Beetstra ^{T C} 14:14, 21 May 2009 (UTC)

Gone through some of the missing chemicals (not redirects), and we actually have such chemicals as articles. I have created a few redirects. Point to note is that many entries are not "proper" grammatical chemical names, which might account for why they are not in WP at all... --Rifleman 82 (talk) 14:44, 21 May 2009 (UTC)

I agree, some of the names are not so useful. Perhaps we should prune the lists and remove items that won't make sense. (In the end, I could probably go through the removed names and add them to our stop word list if applicable.) MichaK (talk) 07:44, 22 May 2009 (UTC)

(ec) Great work! Thanks a million for running the study. Personally I am surprised by the figure of 20,000 articles about "chemicals": less than a week ago, I estimated the figure at about 10,000! Obviously it depends on what you define as a "chemical", and many of the articles are better dealt with by WP:PHARM (for the drugs) or WP:MCB (for the proteins, genes, etc.): I suggest that the study is cross-posted to those two projects, who would doubtless be interested.

Re the 20,000: I counted the number of page titles that match chemicals (>3 chars). So the order of magnitude is probably fine, as some of the matching names will be redirects (and I will also have false negatives). MichaK (talk) 07:44, 22 May 2009 (UTC)

We also have the Common Chemistry list of substances which have been mentioned in more than 1000 scientific papers. The way that we've been running the verification process makes it impossible to give accurate statistics about our coverage levels – the systematic biases are too large – but my best rough guess is that we are missing 20–30% of the compounds, a proportion which is comparable (in every sense) to that found by MichaK for PubMed/PubChem entries. Hopefully we can have another verification drive this summer against the CAS list (I realise that many people are tied up with exams or examining at the moment), and get a similar list of "missing articles". Physchim62 (talk) 14:53, 21 May 2009 (UTC)

Maybe someone could whip up a JS gadget to make creating these redirect pages easier? shoy (reactions) 16:08, 21 May 2009 (UTC)

I'd be careful, as there are definitely some stereochemistry/synonym mismatches in there, so the redirects should be carefully checked. Also here it would probably be good to remove the names that won't make good redirects from the list. MichaK (talk) 07:44, 22 May 2009 (UTC)

Water glass

I looked for water glass and stubled upon the article Potassium silicate. This article needs help! My lectures on water glass are long gone, but I know that the production and the chemistry of sodium silicate is nearly identical to that of Potassium silicate. Would be good if somebody helps. --Stone (talk) 21:31, 23 May 2009 (UTC)

New survey on toxicology info

There was an interesting survey recently on how much people trust toxicology-type info on Wikipedia vs other sources. I wasn't aware that we really handled such information much, but despite that, it appears that we rank quite high! Physchim62, I think you need to get that safety database polished up! See Andrew Lih's blog on the issue. Walkerma (talk) 21:35, 24 May 2009 (UTC)

Yes, we do! It's just we call it "chemical safety" or "hazards" and we use a slightly wider definition than the Society of Toxicology. That's yet another flattering study (full results here), especially coming from professional toxicologists. The detailed results are a little ambiguous – I'll have to contact the authors to see if I can get some more details – but my interpretation is that the respondents were mostly happy with what they see, felt that more info could be added in some cases, and noticed some scare stories. We should be in the Signpost again this week! Physchim62 (talk) 11:52, 25 May 2009 (UTC)

Water fluoridation is a featured article candidate

After many edits, Water fluoridation (edit | talk | history | protect | delete | links | watch | logs | views) has been renominated as a Featured Article. The article's Implementation and Mechanism sections cover the chemistry of water fluoridation. Please feel free to leave comments; instructions for commenters can be found at WP:FAC. Thanks. Eubulides (talk) 00:29, 28 May 2009 (UTC)

Amino acid structure formulae

Hi, I've been browsing the amino acid articles lately, and I noticed the lewis formulae lack a consistent style. At least for those amino acids that allow it, I think it would be a good idea to implement some basic guidelines, like having all structural formulae horizontally aligned, with the amino group showing down and the carboxyl group showing left. This seems to be the tentative standard for most amino acids - look at Glutamine for instance if you want to see what I mean. However there are some which do not yet abide to this rule, like say asparagine. Also some α–amino acids show the hydrogen atom which is bound to the α–carbon, which is redundant even with respect to isomery, since the position of the C-C bonds unmistakably indicates that of the C-H bond.

That being said, I find this would be a considerable improvement, and I would gladly take care of it myself, but I lack any knowledge of how to produce lewis formulae save for painstakingly drawing them out with the gimp. Also for greater consistency the 3D structures might also need to be updated in several cases.

Chymæra (talk) 18:32, 1 June 2009 (UTC)

Hi, Chymæra, I agree. The Lewis formulae lack a consistent style additionally regarding the stereochemistry. For alanine and methionine the structural formulae do not include any information on the stereochemistry. On the other hand the structural formulae of lysine and proline clearly indicate the L-configuration [in both cases (S)-form]. The reason may be: D-alanine is found in proteins of several bacteria, DL-methionine ist an important (> several billion $ turnover per year) product of the chemical industry and used as fodder.– This is not a consistent style! Best regards, --Jü (talk) 19:26, 9 June 2009 (UTC)

Category:Chemical pages needing a CAS Registry Number

Just a question: Shouldn't Category:Chemical pages needing a CAS Registry Number be hidden? --ἀνυπόδητος (talk) 15:12, 4 June 2009 (UTC)

Probably. It is now in any case!  Done Physchim62 (talk) 15:18, 4 June 2009 (UTC)

Thanks --ἀνυπόδητος (talk) 15:24, 4 June 2009 (UTC)

Depiction of racemic compounds

Hi everyone,

I've noticed that User:Jü has been adding some nice PNG (semi-)skeletal formulae to articles on racemic compounds, mostly drugs.

I thought it would be a good time to dicuss how best to show these.

Jü prefers to show both enantiomers explicitly (e.g. http://en.wikipedia.org/w/index.php?title=Fluoxetine&oldid=294762200), while I find this a bit cumbersome and prefer wavy lines (e.g. http://en.wikipedia.org/w/index.php?title=Fluoxetine&oldid=292958306)

What does everyone else think?

Ben (talk) 16:19, 6 June 2009 (UTC)

Most bioactive compounds (e.g. drugs, biomolecules) are single enantiomers, although other editors are more experienced with this area. So any debate centers on "routine" organic and inorganic things. In such cases, I lean toward not depicting both enantiomers except for (i) introductory articles, (ii) famous cases such as Pasteur's tartaric acid (is that what he crystallized?), thalidomide, etc. and (iii) when the structures are confusing (e.g. when no atom is stereogenic). Following (iii), I drew both enantiomers for Co(ethylenediamine)₃]³⁺ and trans-1,2-Diaminocyclohexane, and 1,2-diphenylethylenediamine (all three stereoisomers are shown including meso).--Smokefoot (talk) 16:54, 6 June 2009 (UTC)

That all sounds very sensible. I just don't think there's a need to routinely draw both, as it takes up a lot of space and doesn't add much.

Ben (talk) 20:15, 6 June 2009 (UTC)

I think depicting both enantiomers is quite confusing for the casual reader (or the reader with, say, a secondary-level knowledge of chemistry). Since wavy lines have also elicited some complaints (or... requests for clarification :), I'm not sure which way we should go. Perhaps not note chirality at all for racemic compounds? Fvasconcellos (t·c) 00:35, 9 June 2009 (UTC)

This is a tricky one! It also has major repercussions for our validation effort - these kinds of structure drawings can give rise to major problems, as when C&E News uses Wikipedia for a structure - in that case an error arose from a chiral natural product being represented with an unspecified chiral center. Let's be vigilant! However, with a synthetic molecule it's different; some modern drugs may be defined as one enantiomer, but older ones like ibuprofen are not. Wavy lines aren't the perfect answer, because they don't indicate a racemic mixture; there is (unfortunately) no standard way to represent a racemic mixture in a single structure! I think the "least of all evils" is as FV proposes, to use the "unspecified" notation seen at File:Fenoprofen.png, but I strongly believe that the racemic nature of the compound should be clearly indicated with words somehow. As for representing racemic mixtures of compounds with multiple chiral centers (where relative stereochem is fixed) - I'm really not sure what the answer is! Walkerma (talk) 03:50, 9 June 2009 (UTC)

In general, I don't think we should putting multiple molecules in the infobox. I agree with Fvasconcellos that it "is quite confusing for the casual reader". I think that if the molecule is sold as a single isomer or that's how it appears in nature, then that's the enantiomer we should show. For racemates, I think it's best to leave the stereochemistry unspecified and not use squiggly bonds as those are confusing. For Fluoxetine, what if we just didn't show the benzylic hydrogen? Lay users wouldn't know the difference, chemists would either assume it's a racemate or look at the IUPAC name below it and see that it's (RS)-N-methyl... For Thalidomide I'd just turn that squiggly bond into a regular bond (i.e. not a wedge but a regular "—"; and for Trans-1,2-Diaminocyclohexane I'd just pick one of the two molecules depicted and note in the text that it's a racemate and maybe include a drawing of the two enantiomers in the article, just not in the infobox without explanation. I'd reserve squiggly bonds only for molecules with molecules with multiple stereocenters in which many are always R or S but one or a few are variable. Those are the ones I'd use squiggly bonds on. That's my $0.02. Yilloslime ^T_C 04:14, 9 June 2009 (UTC)

I asked Jü to participate in this discussion. --Leyo 06:40, 9 June 2009 (UTC)

Hi everyone, thanks for your interest. My focus is on drugs, not on stereoisomers (e. g. racemates, enantiomers) in general. Drugs are always used in a chiral environment (e. g. human body). In such a situation a racemate is recognized as a mixture of two different compounds, with a very limited number of exeptions. Racemic drugs may be rated as compounds with 50% impurities. [Ariëns EJ: Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology, Eur. J. Clin. Pharmacol. Volume 26 |issue=6 |pages=663–8 (1984)] This is also the view of the Food and Drug Administration (FDA). Thus, todays separate clinical studies must clearly prove the equevalence of both enantiomers of a new active ingredient of a drug before FDA approval. In >>90% of the active ingredient the pharmacology and the pharmacokinetics of the enantiomers is significantly different. Thus, almost all modern chiral drugs are only FDA-approved as single enantiomers. Drug companies marketing "old" chiral drugs as racemates try to avoid the public discussion of this topic for obvious reasons. Best regards from Germany --Jü (talk) 10:00, 9 June 2009 (UTC)

I would suggest to generally depict only the active (or more potent) stereoisomer and to mention other isomers and their properties, if important, in the text or as a caption. Cacycle (talk) 15:29, 9 June 2009 (UTC)

Hi Cacycle, an example for your suggestion would be Tranylcypromine. In the en:Wikipedia the IUPAC name is: (1R,2S)-2-phenylcyclopropanamine. However, this name is not correct. Tranylcypromine ist a 1:1 (racemic) mixture of (1R,2S)-2-phenylcyclopropanamine AND (1S,2R)-2-phenylcyclopropanamine [Literature: (a) The Merck Index, (b) Axel Kleemann, Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances, 4. Edition (2000) 2 volumes, Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9]. Thus, the structural formulae is also not correct, showing only one enantiomer (1R,2S). As a result, there is some confusion. Best regards from Germany --Jü (talk) 16:25, 9 June 2009 (UTC)

Reliable source for chemical data?

The Open Notebook Science Challenge is used as a reference for solubility data in the chemboxes for a number of chemicals. (Links to oru.edu) Does this meet Wikipedia's criteria for reliable sources? ChemNerd (talk) 14:59, 9 June 2009 (UTC)

This project appears to be an excellent mechanism for teaching chemistry, so well done. Also, it is impressive that this project is associated with the discovery of new drugs with a humanitarian motivation.

In Wikipedia we (IMHO) have a distinct humanitarian mission: creating an encyclopedia of straightforwardly reliable, neutral, and easily verified information. That task is daunting. Wiki-Chem should respectfully decline this offer, because the verification of their data is highly non-standard (encyclopedias are conservative - literally). Our readers rely on editors to use intensely vetted data of the type that NIST, the CRC Handbook, and the Merck Index provide.

The preliminary actions by participants in this project have been unimpressive. This past weekend, the solubility of formic acid in methanol was inserted (at Formic acid) as being 25.6 M. Formic acid is miscible in methanol, so 26.5M is the solubility of formic acid in formic acid. So the Open-Notebook-Science-Challenge-editor that inserted this datum did not exercise good chemical sense (not an evil act, but we don't want that kind of data). Further reflecting the lack of common sense is the seeming random aspect to data insertion. The Open-Notebook-Science-Challenge-editor inserted methanol solubility data for a seeming random collection of organic cmpds, e.g. 4-methylbenzaldehyde. So, with much respect to the Open-Source project, I recommend that we decline the offer.--Smokefoot (talk) 01:36, 10 June 2009 (UTC)

In that case, I'll remove the data and links soon if no one objects. ChemNerd (talk) 18:46, 10 June 2009 (UTC)

Using Jmol on wikipedia and other WMF projects

Please take a look at Wikipedia talk:Using Jmol to display molecular models and join in the discussion. Is there a demand for this? We need to resolve this once for all. --Bduke (Discussion) 23:28, 9 June 2009 (UTC)

GA class

Isn't it about time that this WikiProject starts using GA class? Axl ¤ [Talk] 11:04, 12 June 2009 (UTC)

No. Why? Physchim62 (talk) 11:13, 12 June 2009 (UTC)

Why not? :) Fvasconcellos (t·c) 11:38, 12 June 2009 (UTC)

Currently the rating system is inconsistent and confusing. For example "Talk:Benzodiazepine" notes the article as GA standard. WikiProjects Pharmacology and Medicine also indicate that. So why doesn't WikiProject Chemicals? As first glance, I guessed that it was an oversight. After I "corrected" it, another editor reverted, pointing out that WikiProject Chemicals does not use this standard. Good article status is widely accepted throughout Wikipedia, as evidenced by the number of GA articles and the number of WikiProjects that subscribe to the standard. I reviewed this Project's guidelines and I see no good reason why the Project does not endorse the standard. "Historical" is not a good reason. Axl ¤ [Talk] 15:53, 12 June 2009 (UTC)

I don't see the need to add GA-Class, since it represents an assessment outside our control, and the status of an article as GA is clearly indicated anyway. We may well have GAs that are A-Class, and I suspect we will want to keep them as A-Class. There is an ongoing debate over GA-Class at WP:1.0, and it's certainly a possibility (nothing more) that GA-Class may get abolished in a year or two, for the same reasons - we'll have to see how the new 1.0 bot works out (it records GA/FA status separately from the assessments, obviating the need for GA-Class). However, there is certainly an argument for aligning ourselves with most other projects, and I raise a big fuss if there is a clear consensus here for us to adopt GA-Class. Walkerma (talk) 16:43, 12 June 2009 (UTC)

I should also clarify - we DO recognize GA status (and I've even done GA reviews myself), we simply don't incorporate GA-Class as a separate level in our assessment scheme (for the reasons given). Walkerma (talk) 04:18, 13 June 2009 (UTC)

Benzodiazepine illustrates the problem very well. At it stands, there is no quick metadata to show that anyone from WP:PHARM or WP:MED has ever reviewed that article. On the other hand, it is instantly clear that someone from WP:CHEMS has come along and rated it B-class. Placing GA-class in the WikiProject banners is not only superfluous – there's already a separate banner which lists community-wide assessments – it actually destroys useful information. There are also more technical reasons for not mixing WikiProject and community assessments – apples and pears – which I can explain if you're interested, but I can assure you that it's a Bad Idea and one that we have avoided here. Physchim62 (talk) 23:22, 12 June 2009 (UTC)

"There is no quick metadata to show that anyone from WP:PHARM or WP:MED has ever reviewed that article."

— Physchim62

Someone (or more than one person) at some time must have decided that the article belonged within those Projects' auspices. Are you suggesting that the people adding those banners might not understand whether the article does actually belong? If so, your suspicion is no different from that of the WP:CHEMS banner endorsement. Such boldness can easily be discussed and reverted if necessary. The other problem (that you seem to be implying) is that the assessment might not have been done by "someone from WP:CHEMS". The only qualification required is "simply list yourself at #Participants". Eliminating the GA standard does not address this problem at all. The only valid reason for avoiding the GA level is if the Project does not accept the WP:GAC process. The GA criteria are fairly well described and GA reviews are generally very good. Of course, mistakes sometimes happen. However the assignment of "Stub", "Start" and "B" is also potentially prone to error.

I re-iterate: the only valid reason for avoiding the GA level is if the Project does not accept the GA process. Axl ¤ [Talk] 06:23, 13 June 2009 (UTC)

All assessment is prone to error! You're at WT:CHEMS, you think we don't know a little bit about analysis!

WikiProject assessments are essentially internal assessments, although they provide pretty useful metadata for outsiders as well. WP:GA is an external assessment. It is senseless to combine them on the same scale: as I pointed out above, it leads to the destruction of information. GA nominations are a very useful external check on a WikiProject's assessment scheme, but they are in no way inherently "better", whatever that means. Physchim62 (talk) 11:18, 13 June 2009 (UTC)

Another important point is that a given article need not have the same assessment for all wikiprojects to which it belongs. A given article could be excellent from the point of view of art, history, pharmacology, economy, or sports, and yet be poor from the point of view of chemistry. --Itub (talk) 12:48, 13 June 2009 (UTC)

I have two questions. --- One on the difference of GA and FA. Am I right with the asumption that both are external and do not require a input from the project. This would make it logical to treat them both the same, or is it the case that FA needs project participation which would make it different to GA. --- The second question is on the difference in rating in different projects. I thought that this should only be possible in the system Stub, Start .... A-Class, in the GA and FA system only articles with a full coverage on the subject would be listed as GA or FA and if the chemistry part would be missing a reassessemnt and and a delisting would follow. ( Sorry WPchemistry and WP chemicals friends, but friend told me that the Des hamma imma sho so g`macht (We did it all the time that way.) is no justification for a anything.) I also got the notice once that due to historical reasons ... and to replace this phrase with a good argument would be the best outcome of the discussion. --Stone (talk) 14:50, 13 June 2009 (UTC)

The WikiProject member has no defined qualifications to prove a more accurate assessment than that of the GA reviewer. Indeed the GA reviewer explicitly should be an uninvolved person: "you cannot review an article if you have made significant contributions to it prior to the review". In my opinion, this makes the GA review more legitimate than the WikiProject member's assessment.

You haven't shown what information is "destroyed" by including GA in WikiProject banner. Axl ¤ [Talk] 17:25, 13 June 2009 (UTC)

To Itub, are you referring to articles that fall within the purview of more than one WikiProject? If so, the GA criteria includes the need to be "broad in its coverage". If the article belongs with only one WikiProject, your point is irrelevant. An example article would help. Axl ¤ [Talk] 17:29, 13 June 2009 (UTC)

Uninvolved for review can also be the person which has not the slightest knowledge about the important facts. So the project will have the best people to do the review. In nearly all the GANs an all the FACs I had the pleassure to participated where done in a way that members of the team were part of the review. Without the knowledge and the help of the projects most of the reviews would be pointless.--Stone (talk) 17:51, 13 June 2009 (UTC)

Is there another project without GA?--Stone (talk) 17:51, 13 June 2009 (UTC)

Replying to Axl, a good example is Diamond, which despite being a FA for years wasn't even worth a C-class in chemistry IMHO until sometime last year, when someone finally thought of adding a picture of its chemical structure! This is the most "elemental" fact about diamond, something you will find in every general chemistry textbook because it is one of the most paradigmatic crystal structures. It is currently rated start-class in chemistry, but I think that's a bit low. I agree that this point is irrelevant if an article belong only to this wikiproject; I wasn't providing a full argument but just adding one point to those made by others. But briefly, my problem with GA class even in those cases is that the GA review focuses on very different things than the wikiproject assessment, which makes the two assessments non-comparable (which among other things leads to silly debates such as whether A-class should be higher or lower than GA-class). --Itub (talk) 13:00, 15 June 2009 (UTC)

The argument that the two scales are non-comparable is the best I have heard till now. With this reason I can live. So after becoming a GA I simply can ask the project what it takes to improve the article to A-Class. A ranking identical in all projects would be better, but if there is a reason for the difference it is OK.--Stone (talk) 14:38, 15 June 2009 (UTC)

Itub, thanks for your reply. It is interesting to see that "Diamond" has been rated as FA standard by the FAC reviewers, yet it remains "Start class" according to WP:CHEM. "Diamond" has actually been rated by the parent project WikiProject Chemistry, not WikiProject Chemicals. (WikiProject Chemistry does use the GA standard.)

I see that you didn't upgrade the article's WP:CHEM rating, despite your possible disagreement with the current rating. I wonder why not?

One of the requirements of a featured article is "it neglects no major facts or details". Of course the FA reviewers don't necessarily have specialist experience of the article's topic so it is possible for such details to be missed. When another editor finds a featured article that omits a major detail (such as chemical structure in the article "Diamond"), there are two appropriate courses of action:-

1. Add the detail, possibly with assistance from other editors such as those from a relevant WikiProject.
2. Take the article to FA review. (Actually someone has indeed taken the article to FA review.)

"The GA review focuses on very different things than the wikiproject assessment."

— Itub

WP:CHEMS has contradictory statements about its scope. The lead section states that WikiProject Chemicals "concerns writing and improving articles about chemical compounds in Wikipedia." Later in the text, the page states "This comprises all organic and inorganic compounds, elements, reagents, commodities, pharmaceuticals, pollutants, and other large-scale and small-scale chemicals of interest", not just chemical compounds.

In any case, the main point seems to be the article's title. If the article is about one of these compounds, elements, etc., it falls within the scope of the WikiProject.

The WikiProject claims to aim for "standardized articles". To do this, you need a style guide. Ironically, Wikipedia:WikiProject Chemicals/Style guidelines "is currently inactive and is retained for historical reference. Either the page is no longer relevant, or consensus on its purpose has become unclear."

Your project does not define "start class", "stub class", etc., so presumably you follow the generic guidelines at "Wikipedia:Version 1.0 Editorial Team/Assessment"? If you follow those guidelines, why aren't you also following their GA guidelines? Axl ¤ [Talk] 10:21, 16 June 2009 (UTC)

I don't understand the point of this nitpicking. "Chemicals" is used loosely, and includes all the items listed (although elements have their own subproject). As for the style guide, the page you linked to is historical because the style guide was moved and reorganized into Wikipedia:Manual of Style (chemistry) as the very first line in the old guide says. As for whether diamond is "chemicals" or "chemistry" or "elements": these three wikiprojects have largely overlapping membership and we don't tend to lose sleep if the subdivision between them is sometimes loose. --Itub (talk) 11:42, 16 June 2009 (UTC)

What do I mean when I say that GA and project ratings focus on different things? I'm not talking about the nice colorful table you link to--I'm talking about reality. In reality, GA and FA tend to focus on whether the article uses non-breaking spaces and en dashes, whether the images have the proper templates attached, and whether every sentence has a footnote whether sensible or not. Important things surely, but not the main area of interest to a chemist who wants to add content to Wikipedia. --Itub (talk) 11:53, 16 June 2009 (UTC)

The point of this "nitpicking" is to establish the purview of this WikiProject. How does the scope of WikiProject Chemicals differ from that of WikiProject Chemistry? Does "Diamond" belong in the purview of WikiProject Chemicals? If so, why haven't you added a WP:CHEMS assessment class? What should its class be?

"The style guide was moved and reorganized into Wikipedia:Manual of Style (chemistry)."

Exactly! WikiProject Chemicals uses the same style guide as WikiProject Chemistry. So why doesn't it use the same assessment grading?

After some digging around, I found WikiProject Chemicals' assessment system. It is unclear to me if this system is used or not. It is not linked from the WikiProject's page. It includes an Importance scale, which is explicitly not used. Also, you didn't mention it when I questioned the WikiProject's standards for assessment. Wikipedia:WikiProject Chemicals/Assessment is inconsistent with its own project's front page.

I still don't know how you assign class ratings. Axl ¤ [Talk] 18:08, 16 June 2009 (UTC)

mostly silently, without causing a fuss. I do a lot of article assessments for WP:CHEMS, and typically do the following:

1. Is this article really about a single chemical compound? If not: change chemicals to chemistry template
2. Does the article contain enough chemical data to warrant stub/start/B/A class according to the WikiProject Chemicals' assessment scale (ps. Did you know that this list was the original of the current WP general assessment scale!)
3. Has this article become Featured because of or in line with the WP:CHEMS effort?
4. How large is the impact of the chemical compound in chemistry (could be world production, could be historical value, could be contribution important chemical reaction/theory, etc)?

I've done a few thousand assessments sofar (interesting reading), and this works quite effectively. Wim van Dorst (talk) 22:05, 16 June 2009 (UTC).

Thank you, Wim van Dorst. Perhaps you would consider adding this process to the WikiProject's front page, including a link to the assessment scale? I'm still unclear why the FA standard is endorsed while the GA standard is not. In any case, if the WikiProject's consensus is that the GA standard should not be endorsed, then so be it. Axl ¤ [Talk] 12:41, 17 June 2009 (UTC)

You make a good point about FA class. Indeed, I was thinking of proposing that we remove it from our assessment scale, as I did when I wrote the assessment scale for WP:MEASURE. When the assessment system was conceived, we never thought that here would be articles from this project going to WP:FAC without first being A-class: however, FAC has become much more individualist since then.

On the other hand, you reiterate the claim that this project "does not endorse" the GA standard. Of course we endorse it, we simply don't include it in our project tag. None of the comments above have anything to do with attacking the idea of WP:GA, we have simply pointed out that the relevant information is already included on the article talk page, and so does not need to be repeated by how ever many times there are WikiProjects that tag the article. Physchim62 (talk) 13:05, 17 June 2009 (UTC)

I see, thank you. Axl ¤ [Talk] 20:09, 17 June 2009 (UTC)

proposed infobox entry

I suggest having an entry called "Stability" on EACH chemical; this could be for example: (1) stable in air; (2) stable in the presence of O2, unstable in the presence of H2O; (3) stable in the presence of H2O, unstable in the presence of O2; (4) stable under inert gases up to -x oC; etc. Nergaal. 18.74.7.239 (talk) 15:13, 17 June 2009 (UTC)

I think you're right that every chemical article should cover this topic; however, I think the place to cover this is under the "Properties" section. There are various parameters to consider (IMHO), making it difficult to reduce stability to a simple infobox entry:

Variable range

Stability (or lack thereof) is quite a variable concept, covering a huge range of reactivity; if we're talking about a highly reactive substance like cyclobutadiene it has a different context than if we're talking about the stability of alkanes during cracking.

Kinetic vs thermodynamic

Diamond is kinetically stable (over a human lifetime), but thermodynamically it is unstable with respect to graphite. We want to make sure we don't mix apples and oranges; hexane is stable in oxygen until you put a match to it! Including things like flash point and explosive limit in the article can explain such information systematically.

Different types of stability

Nitroglycerin is stable until you bump it - would that class as stable, or not? What about something like diisopropyl ether, which is (or at least was) commercially available and widely used in the open lab - this can form an organic peroxide in the air within a couple of days (I'm told) which makes the solvent shock-sensitive. And many amines are "stable" yet absorb carbon dioxide from the air to form annoying crystals. In short, we might have something "stable" by one measure but unstable by another.

Can we agree to cover the topic under "Properties", and amend the relevant section at Wikipedia:Manual of Style (chemistry)/Chemicals accordingly? Cheers, Walkerma (talk) 16:52, 17 June 2009 (UTC)

Bromo-aniline

Cleanup on aisle 5 :) Fvasconcellos (t·c) 20:10, 20 June 2009 (UTC)

Found a crystal structure, CrystEngComm (2003) 5, 248-252, image on the way.

Ben (talk) 21:25, 20 June 2009 (UTC)

It does probably not matter for bromoaniline, but in general I am strongly opposed to using crystal structures for slightly larger or more flexible molecules than this! Crystal structures have often strange conformations that differ considerably from (hand-)minimized structures as well as from the biologically active conformations in case of drugs. A bad and illustrative example I noticed recently is tetrahydrocannabinol. Reasons for such strange distortions are intermolecular interactions and hydrogen bonds in the crystal as well as packing effects. Crystal structures are perfectly fine for illustrating salts, complexes, and proteins, but we should not use them for normal organic molecules. Cacycle (talk) 05:34, 21 June 2009 (UTC)

Ben's impact has been huge, but I agree that for most organic things, crystal structures are more confusing than enlightening. And sometimes misleading even.--Smokefoot (talk) 01:57, 23 June 2009 (UTC)

All structures can be misleading if one doesn't consider the context in which they were obtained! I don't think crystal structures of organic molecules need to be singled out. --Itub (talk) 11:42, 23 June 2009 (UTC)

Where else are we going to get the structure from?

Ben (talk) 08:16, 26 June 2009 (UTC)

You can either use a modeling kit and a camera :-) or a molecular modeling software (e.g. Chem3D). You change torsion angles by hand to get a meaningful conformation with respect to minimal (steric) energy (also look for intramolecular interactions such as hydrogen bonds), didactic purpose (should be easy to understand in a 2D image), and to possible biological, physical, or chemical activities or actions. Then you could optionally minimize the molecule or try to test alternative conformation with the least energy. But I consider the last part optional, standard angles and bond lengths are good enough for our purposes. Cacycle (talk) 21:31, 26 June 2009 (UTC)

That's too prone to mistakes, though, isn't it? Works OK most of the time, but then you have things like aniline, where your might wrongly make the nitrogen atom sp². I think this "do it by hand" method is more questionable than any effects crystal packing etc has on conformation.

Minimisation could be the way forward. Hmmm. I'm just not happy with any of the solutions at the moment, including my own favourite (crystal structure).

I just calculated the structure of 4-bromoaniline in Spartan: PM3 and HF 3-21G wrongly give planar nitrogen, while HF 6-31G* correctly gives pyramidal N. Much easier to just go straight to the crystal structure rather than spend 30 minutes calculating it - and if the molecule had a few more atoms, I would've been unable to use 6-31G* and would therefore have got the wrong structure.

Ben (talk) 07:41, 27 June 2009 (UTC)

We dont need ORTEPs or packing diagrams from small molecule crystallography. We absolutely need such images from extended systems.--Smokefoot (talk) 13:08, 27 June 2009 (UTC)

Yep. For most organic compounds, it's the structure of the molecule itself that's of interest. The packing and all that is usually just irrelevant/confusing - except when discussing crystal engineering or whatnot. I just use crystallographic data to get the true structure of the molecule, because quite often, intuition or Spartan give the wrong answer (e.g. geometry of nitrogen in anilines).

Here's an example. Pethidine is very topical at the moment (apparently Michael Jackson was taking it when he died). It doesn't have a 3D image. I've got the crystal structures of the hydrochloride and hydrobromide from 1974. I thought I'd take the molecule from one of those, and minimise it in Spartan. However, I only have the student version, which has the following size limits:

• Molecular mechanics: no limit
• Semiempirical (PM3): 75 atoms
• Hartree-Fock (STO-3G, 3-21G, 6-31G* and 6-311+G**): 30 atoms
• DFT: B3LYP: 30 atoms
• MP2: 20 atoms

Since pethidine has 39 atoms, the best calculation I can do is PM3.

I think pethidine is probably too complicated to analyse by rotational spectroscopy, so can't use that to get the structure (but microwave is great for things like HCO⁺).

Does anyone have any suggestions for pethidine? What is the best structure to present?

Ben (talk) 14:25, 27 June 2009 (UTC)

Proposal to remove FA-Class from our Assessment Scheme

In our Assessment Scheme, we recognize Stub, Start, B and A Classes for chemical completeness of a WP:CHEMS article (worklist or not). Additionally to that, we have also the FA-Class which was originately considered as an A-Class article (with regard to it chemical completeness and quality), but having received the FA-Status as well. Now with other WikiProjects working on articles that also fall in the WP:CHEMS remit, it may well be that an article is Featured, although it doesn't have sufficient chemicals information in it for A-Class status yet. Therefore I propose to remove FA-Class from our WP:CHEMS Assessment scheme. Wim van Dorst (talk) 23:17, 22 June 2009 (UTC)

• Support Wim van Dorst (talk) 23:17, 22 June 2009 (UTC) (proposer)
• Support --Smokefoot (talk) 01:57, 23 June 2009 (UTC)
• Support Thricecube (talk) 04:23, 23 June 2009 (UTC)
• Support. However, it would be nice to teach the bot that updates the summary table to produce a separate table counting how many articles have FA and GA in case anyone cares. --Itub (talk) 11:40, 23 June 2009 (UTC)
• Support to be consistent within the project, but an incorporation of GA would also get my support.--Stone (talk) 12:49, 23 June 2009 (UTC)
• Support as per the discussion with Axl (talk · contribs) above. These are different, and hence complementary, scales: they shouldn't be mixed. WP:MEASURE has already removed FA-class from its project assessment scheme for exactly this reason. To reply to Itub, yes, we can fairly easily follow our GAs and FAs without including them in the project assessment scheme. Physchim62 (talk) 13:31, 23 June 2009 (UTC)
• Oppose. Support. Thanks for comments below. (But I am open to change my mind if my concerns can be ameliorated.) The goal of getting articles up to FA status has been a motivator for me to work on some at length (most fervently PFOA). So I oppose the removal of this carrot. I understand we can, but I'm not convinced we should. FA are a central theme here on WP, as one is "featured" daily on the main page. Could a compound (or compound class) be promoted to FA without being subsumed under another project? I noticed the HCl page and it is on the Version 1.0 Editorial Team (not familiar to me) list, so it won't get demoted if this proposal is accepted? Is it any more difficult than a regular FA review to be on a "Version"? I oppose what looks like a trade in of a widely recognized and WP celebrated incentive in return for what appears to be an isolationist statement of independence to get a mere notch of simplification on a grading assessment. -Shootbamboo (talk) 03:11, 24 June 2009 (UTC)

• You can still get an article featured, regardless of whether it belongs to this project or not. It doesn't even need to belong to any project. The only thing that would change under this proposal is the rating that would be shown in the wikiproject chemicals box (and the relevant categories and tables). --Itub (talk) 13:33, 24 June 2009 (UTC)
• As pointed out by Itub, indeed the greater WikiPedian goal of Featuring all articles, with the pertaining quality requirements and procedures, remain to be endorsed by the WikiProject. Promotion for GA and FA remain completely the same, and all articles remain to have FA status. The proposal here is to have the WP:CHEMS classification limited to what WP:CHEMS is about, viz., chemical completeness of the article. Just consider them separate, autonomous qualifications of the articles. Wim van Dorst (talk) 19:49, 24 June 2009 (UTC).
• I've tried to stay out of this debate, since I'm too involved with the 1.0 scheme community-wide, but perhaps I can make a few comments! I am happy to work with the system with or without FA-Class as part of the assessment scale. Clearly we will still participate in trying to get articles up to FA standard, as (for example) Wim has done admirably in the past. What I can say is that we at WP:1.0 will make sure we score any FA article tagged as A as being the same as FA-Class. This will be especially easy when the "second generation" 1.0 Bot comes out soon, and it will indicate all FAs and GAs regardless of their assessment tag. Walkerma (talk) 20:01, 24 June 2009 (UTC)

You've got a few weird things going on here. There's currently a good Start-Class article and a featured B-Class article. Surely these need looking at? Regards, — Martin (MSGJ · talk) 12:12, 26 June 2009 (UTC)

Hmm, is that really the problem of this project? Benzylpiperazine Start-Class because there's virtually no chemistry in there at all. Bupropion is B-Class because there's more chemistry which could be added reasonably easily. Yes, we should improve both these articles, and about 5000 others! You're not complaining to WP:FA or WP:GA because there are articles which they think are excellent or good, but which we disagree… WP:CHEMS is not responsible for any failings in the quality assurance procedures at these central processes, much as we try to help. The difference with this new system is that we can spot such failings much more easily ;) Physchim62 (talk) 12:26, 26 June 2009 (UTC)

I'm not complaining. I was merely curious about it and wanted to check that it was intentional. I look forward to the first featured stub!! — Martin (MSGJ · talk) 12:47, 26 June 2009 (UTC)

Both article lack most of the chemical information to get it to above B-Class. So the a featured stub would be no problem looking at that articles.--Stone (talk) 18:56, 27 June 2009 (UTC)

Following the concensus above, I have now re-assessed all seven formerly FA-Class articles to A-Class. The {{chemicals}} template was already partially adapted to show FA-Class as A-Class effectively. Thanks, Martin! And I like the (A) logo! Wim van Dorst (talk) 21:44, 29 June 2009 (UTC).

Bupropion was also formerly FA-Class, but I had already reassessed it to B-Class (for this project) because of its lack of chemistry. It's a decent article, if anyone fancies expanding the Synthesis section a bit we can have another look at it. Physchim62 (talk) 22:08, 29 June 2009 (UTC)

Maybe I'll get flamed for being a WikiProject stalker, but if those articles are missing so much chemical information... should they remain FAs? It seems to me that they would fail the comprehensiveness criterion of WP:WIAFA... Titoxd^{(?!? - cool stuff)} 06:15, 9 July 2009 (UTC)

Atomic radii

A comment on the talk page of magnesium (which I couldn't answer to my shame) brought me to this conclusion: the atomic radii in all elementboxes are copied from Atomic radii of the elements (data page), which in turn are copied from webelements.com, which in turn are copied from the articles J.C. Slater, J. Chem. Phys. 1964, 41, 3199 ("empirical") and E. Clementi, D.L.Raimondi, and W.P. Reinhardt, J. Chem. Phys. 1967, 47, 1300 ("calculated)". The data are simply wrong and must be replaced. An easy check would be comparing the "metallic radii" and "empirical" radii at Atomic radii of the elements (data page). Checking the Slater's paper reveals that both are defined in the same way, i.e. half interatomic distance in the elemental solid, but the Slater's values are way off the current XRD data. An easy answer to that is that in 1960s both the experiment and calculation did not have enough accuracy (not only measurements but also sample preparation). People who know me know that I have little tolerance to such blunders :), especially if they turn out at numerous FA and GA element pages. My intention is to (i) delete calculated radii, as they only mislead the reader and are subject to numerous theoretical assumption; (ii) replace the atomic radii in the elementboxes with proper values, which are just half of nearest-neighbor distances in elemental solids at room temperature. Whenever there are several crystalline forms at room temperature, I suggest taking an average value. Materialscientist (talk) 01:51, 24 June 2009 (UTC)

Sodium hydroxide GAR

I suppose this article was written to different standards, but I would say it is deficient today. Perhaps we can have this as the collaboration of July? --Rifleman 82 (talk) 16:24, 25 June 2009 (UTC)

Problem with Mol2Svg

I have noticed that SVG images drawn by Ronhjones have a transparent background but not behind heteroatoms. It seems that there is a problem with Mol2Svg. Who uses this converter and is able to help here? --Leyo 05:44, 26 June 2009 (UTC)

I've given up Mol2svg (it's a free converter from "Chem Solutions" -Russia site) in favour of printing from IsisDraw to EPS and converting with Scribus. I've annotated Wikipedia:Manual of Style (chemistry)/Structure drawing to point out the issues. I've also re-drawn all the ones that had the problem.  Ronhjones  ^(Talk) 19:51, 31 July 2009 (UTC)

Category:Chemical pages needing an infobox

Are articles not automatically added to this category? shoy (reactions) 17:46, 26 June 2009 (UTC)

How do you think that would work? --Leyo 05:55, 30 June 2009 (UTC)

Either a bot, or some parameter in chemistry-related categories? This category would be a lot more useful in finding chemistry articles missing chemboxes if it was automatic. (User:Shoy, public terminal) 136.165.49.113 (talk) 16:23, 30 June 2009 (UTC)

There is a searchbot that finds new chemistry related articles (forgot the name), but until it is recognised as a chemical compound, it is difficult to assess if an infobox is needed. My detection generally starts when an article gains a chemobox/drugbox .. However, a reasonable place to start may be the -compound-stub categories. --Dirk Beetstra ^{T C} 17:52, 30 June 2009 (UTC)

If there were an automated way of selecting articles with {{chemicals}} on the talk page, but no {{chembox}} or {{drugbox}} on the article page, you might come up with a reasonable list. Also, new chemistry-related articles are listed at User:AlexNewArtBot/ChemistrySearchResult. -- Ed (Edgar181) 18:32, 30 June 2009 (UTC)

Thanks, that's a useful page. It seems like a trivial task to write a bot that would create a list like that, Ed, but I'm no programmer. shoy (reactions) 20:30, 30 June 2009 (UTC)

I've created a list at User:Itub/Missing chemboxes. Adding the relevant articles to the category is left as an exercise to the reader. ;-) --Itub (talk) 02:18, 1 July 2009 (UTC)

Wait, the list is not quite right... it includes redirects, which of course don't need a chembox... --Itub (talk) 02:26, 1 July 2009 (UTC)

I've now looked at a pseudo-random sampling of entries in my list, and I think that most entries are legitimate. However, in addition to the redirects, there are some articles that do have an infobox, but that it is neither a chembox nor a drugbox (neurotransmitter boxes, mineral boxes, or whatever...) --Itub (talk) 12:50, 1 July 2009 (UTC)

Thanks Itub, I'll get to adding some chemboxes when I get a chance. shoy (reactions) 16:36, 1 July 2009 (UTC)

Alternative names in lede

• 1) Common lede style: bolded title chemical name, sometimes with parenthetic mention of a common abbreviation if it is used in the body of the article.
• 2) Occasional lede style: in addition to the bolded title chemical name, one or several alternative names (bolded) are also listed.

Suggestion, since the ChemBoxes usually list "other names," it seems that the preferred style is #1. Not a big deal, but we should probably aim for consensus.--Smokefoot (talk) 18:02, 30 June 2009 (UTC)

I prefer option 1 and regularly move uncommon synonyms from the body of text to the chembox. -- Ed (Edgar181) 18:34, 30 June 2009 (UTC)

I like option 1 because it reads much better.

Ben (talk) 09:05, 1 July 2009 (UTC)

Indeed, I'd prefer option 1 as well, bit expanded (for our chemmos?):

• Lede style: bolded title chemical name (generally the same as the article name), with parenthetic mention of common abbreviations and alternative names. Less common abbreviations and alternative names go to the 'Abbreviations' (in the {{Chembox Identifiers}} module) and 'OtherNames' (main part) of the {{chembox}}

With common I mean things like 'ethene' -> common alternative name 'ethylene'.

Similar here, I'd like in the lede also to have 'CH₃COOH' for acetic acid, while 'Formula = C₂H₄O₂' (or 'C = 2 | H = 4 | O = 2' goes into the chembox. --Dirk Beetstra ^{T C} 09:31, 1 July 2009 (UTC)

Copyvio on Ammonium phosphate

Would someone who knows more about this area than I do care to help rewrite this article? As it stands, it's pretty much a word-for-word copyvio from this book. I've already blanked the offending text. shoy (reactions) 19:22, 6 July 2009 (UTC)

As far as I could see only part of the first paragraph was copied from that book. I've restored the article but commented out the sentences matching the book. --Itub (talk) 12:25, 9 July 2009 (UTC)

Chembox new

I need advice of the Project on usage of chembox/chembox new templates, because we are getting into a dispute with user:Plasmic Physics on titanium nitride. All I see in his converting into the chembox new template is loosing "space group" in "structure" section and swelling the pages by unnecessary fields. Am I missing something ?

Another part of the problem is old with the Project, but not with me - the user has 150 WP edits in total, but is keen to rename all chemicals on WP. The example here is "titanium(3+) ion azanetriïde" for "titanium nitride TiN", and it seems he is going around other chemicals. This is worrying to me and this might need a quick reaction. Materialscientist (talk) 11:26, 9 July 2009 (UTC)

Plasmic Physics is a griefer, whom we have contended with previously.--Smokefoot (talk) 11:48, 9 July 2009 (UTC)

Can't we do something? Like ban Plasma Physics? Ben (talk) 13:00, 9 July 2009 (UTC)

I encourage everyone to leave a brief, but clear comment expressing his/her vote on the IUPAC name change by user:Plasmic Physics (and any relevant matters). This will demonstrate the view of the Project and is necessary (and sufficient) to stop such attempts (now and in the future) by standard WP means. As a side note, I would appreciate a comment on "chembox new" and reasons for its existence. Materialscientist (talk) 23:22, 9 July 2009 (UTC)

{{Chembox}} used to be something else, now {{Chembox old}}. {{Chembox new}} was a prototype for the current {{Chembox}}. I've redirected it now - development stopped late last year, and the new box is backward compatible. --Rifleman 82 (talk) 01:50, 10 July 2009 (UTC)

Magnesium chloride needs some attention

Magnesium chloride needs some attention. There's some bogus info there, and someone qualified should read over the entire article as a check. "Liquid magnesium chloride" info is bogus; I think someone meant a solution of the salt in water. The last sentence of the lede makes no sense. And the price of magnesium metal is off by an order of magnitude. There may be other problems; this isn't my field. So I hesitate to fix anything there. --John Nagle (talk) 05:58, 25 July 2009 (UTC)

I believe I addressed all the problems, though the article needs a lot more help - thanks for your comments! Walkerma (talk) 21:12, 25 July 2009 (UTC)

Dry ice

I've been working on improving this article, as part of the spotlight project, but I'm no expert, and I could really do with help.

Specifically, any help with filling in the infobox would be great, and any further info that could be added to the article - anything, really. Cheers,  Chzz  ►  06:23, 31 July 2009 (UTC)

IMHO the infobox should be removed. It is sufficient to have an infobox in carbon dioxide. --Leyo 08:10, 31 July 2009 (UTC)

(edit conflict) With regard to the chembox - I feel strongly that this article should NOT have a chembox because one is already maintained at carbon dioxide. Maintaining two leads to synchronization problems and double-work. --Rifleman 82 (talk) 08:11, 31 July 2009 (UTC)

I agree, no chembox here, that should be on the page of the chemical compound. I believe that we do have a chembox on Water (molecule) (which is the description of the chemical), not on any of the other forms (Steam, Water, Ice, and all the other forms of H₂O that we describe). --Dirk Beetstra ^{T C} 09:28, 31 July 2009 (UTC)

I disagree. The information specifically relevant to the article topic is best presented in an infobox - I carefully did not try to duplicate things that were not relevant. To the degree of rounding used, there is no chance that things like sublimation point are ever going to change. Regarding duplicated work, when has Wikipedia ever worried about having to update articles? MOS says that an appropriate infobox should appear on articles wherever it makes sense, and this seems to be the most applicable infobox - I noted how highly customizable it was. It presents the key data in a clearer manner.  Chzz  ►  16:42, 31 July 2009 (UTC)

I also recommend no Chembox. Otherwise, the article misleads readers in a subtle but significant way, i.e. that CO₂ is dry ice. I am sure that Chzz only wants to help readers by providing information, but I think that Beetstra and others above make a good case for not including it.--Smokefoot (talk) 17:05, 31 July 2009 (UTC)

Hi there. Smokefoot, thanks for your comments - I do understand, and free discussion etc is great. The spotlight group are moving on to the next article about now anyway. I'll put a few comments about future development thoughts, and a note about this chat, on the article talk. Cheers,  Chzz  ►  02:32, 1 August 2009 (UTC)

As we didn't conclude anything here, could someone please add what you do consider to be an appropriate infobox? The article will, eventually, list a great deal of data - thus an infobox would seem appropriate (if it is to reach GA, FA). So - I understand why the box that I added was removed, but could somebody please think of an alternative?  Chzz  ►  03:16, 4 August 2009 (UTC)

Well, Water does not have an infobox, that one is on Water (molecule), I think some data left and right could be small tables, or just mentioned, and the article needs an early link to Carbon dioxide. I hope this explains. --Dirk Beetstra ^{T C} 06:16, 4 August 2009 (UTC)

Propylene oxide vs 1,2-propylene oxide

Recently propylene oxide was moved to 1,2-propylene oxide. The move was well-intentioned and motivated by the creation of an article on 1,3-propylene oxide. I think that this move was a mistake. For those that use or might use chemistry, there (virtually) is only one propylene oxide, the 1,2-isomer. No one who buys or uses or exposed to this stuff calls it anything else. Also editors of WE chemistry articles have over the years given priority to traditional naming (e.g. discussion of acetic acid vs ethanoic acid). Also it seems that in general the term alkene oxide is usually (not always) reserved for 1,2-epoxides. Please register your views on reverting the name change.--Smokefoot (talk) 21:57, 1 August 2009 (UTC)

I much prefer "propylene oxide" because it's easier to type and simpler to remember.

All this 1,2- business is best left for comparisons (e.g. the 1,3- isomer of propylene oxide is trimethylene oxide)

Ben (talk) 23:54, 1 August 2009 (UTC)

I consulted the mover and that person is agreeable to my moving it back, so I'll do that. So Propylene oxide will survive.--Smokefoot (talk) 00:16, 2 August 2009 (UTC)

I moved it (as I agree). Hope all is correct. --Dirk Beetstra ^{T C} 00:35, 2 August 2009 (UTC)

Capitalization of chemical starting with numbers

Recently an editor moved 1,1-dichloro-1-fluoroethane to 1,1-Dichloro-1-fluoroethane (and many others), saying "capitalization of the first word in chemical names that start with a number is the Wikipedia standard". I was not aware of any such standards, and the end result is rather ugly IMO, as it would never be capitalized like that anywhere else. Is this in fact the Wikipedia standard, and why? This doesn't seem to be covered by WP:MOSCHEM. Headbomb {^ταλκ_{κοντριβς} – WP Physics} 16:10, 5 August 2009 (UTC)

WP:CHEMNAME#Capitalization of elements and compounds seems to support the change: "dichloro" is the first real word part of the name, so it gets capitalized at start of sentences and by extension in other situations where "first letter of term" should be capitalized. However, I agree that this issue needs consensus and definitely an explicit statement on MOS somewhere. See also Talk:Gamma-Hydroxybutyric acid/Archive 1#The Title Casing for a similar issue. DMacks (talk) 16:29, 5 August 2009 (UTC)

We have debated this about 3-4 years back, and we agreed then that something like 1,1-Dichloro-1-fluoroethane would be the default format, though we usually like to make a redirect from the other form (though the software is better at handling this issue now). The WP standard is to have article names begin with a capital letter, and as Dmacks says, in chemistry that refers to the "first letter of term". Certainly in a book, any sentence beginning with the compound name would be written "1,1-Dichloro-1-fluoroethane is a compound...." Walkerma (talk) 16:40, 5 August 2009 (UTC)

(ec) This issue is, in fact, specifically mentioned in the MOS at Wikipedia:Naming conventions (chemistry)#Prefixes: "When the chosen article title starts with a number, the first letter of the compound name should be capitalized: hence 1,1,1-Trichloroethane not 1,1,1-trichloroethane." This issue has cropped up many times over the years and there has always been consensus for the way the guidelines are currently outlined in the MOS. This is not just Wikipedia's style, but rather proper chemical nomenclature that is used in chemical catalogs, textbooks, chemical journals (for example, as outlined in the ACS Style Guide), etc. -- Ed (Edgar181) 16:47, 5 August 2009 (UTC)

Nomenclature for molecular formulas in Chembox

It's not clear to the average editor what the appropriate way to write molecular formulas is in a chembox. For example, I read WP:MOSCHEM and WP:CHEMBOX but was unable to determine whether urea should be written CH₄N₂O or (NH₂)₂CO [7]. I'm sure this has been discussed before and consensus has been reached – it's just not clear where to find it. I suggest WP:MOSCHEM should include details on preferred nomenclature, and these details should be linked from WP:CHEMBOX. Adrian J. Hunter^{(talk•contribs)} 14:02, 6 August 2009 (UTC)

There is a similar discussion above (or on the talkpage of the Chemistry project), about this. I would suggest:

• In the text, use '(NH₂)₂CO',
• in the chembox either 'CH₄N₂O', or 'C = 1 | H = 4 | N = 2 | O = 1' (both give practically the same result, the latter is a bit nicer as it also results in the Mw of the compound. I don't think that it is mentioned somewhere.

Hope this explains. --Dirk Beetstra ^{T C} 14:06, 6 August 2009 (UTC)

In my experience, industrial chemists always use the Hill system of writing chemical formulae. Maybe a link to Hill system in WP:CHEMBOX would be in order.  Ronhjones  ^(Talk) 19:23, 6 August 2009 (UTC)

That is indeed also the one that I meant, and it is also the system that the 'C = 1 | H = 4 | N = 2 | O = 1'-programming is following (irregardless of the order of the parameters!). --Dirk Beetstra ^{T C} 19:37, 6 August 2009 (UTC)

Just don't use the Hill System to write HCl as ClH or similar - it looks ridiculous! Ben (talk) 20:46, 6 August 2009 (UTC)

Quite a few inorganics don't look good with the Hill System, but it does work well for organic molecules.  Ronhjones  ^(Talk) 20:38, 7 August 2009 (UTC)

Agreed - can we make that a guideline?

Ben (talk) 21:48, 7 August 2009 (UTC)

Antimony pentasulfide

This stub also misses an image of the structure. Who can add one? --129.132.225.82 (talk) 08:49, 7 August 2009 (UTC)

I'll do it, possibly tonight.

Ben (talk) 17:04, 7 August 2009 (UTC)

According to the article “it is a nonstoichiometric compound with a variable composition”. How would you depict that? --Leyo 06:16, 12 August 2009 (UTC)

With great difficulty. I looked for a structure, found none, then realised.

Probably best left unillustrated.

Ben (talk) 09:13, 12 August 2009 (UTC)

...like many articles on inorganics. Fvasconcellos (t·c) 13:47, 12 August 2009 (UTC)

Tsk. We can illustrate with photographs! --Rifleman 82 (talk) 15:54, 12 August 2009 (UTC)

Tranylcypromine

Can someone have a look at the content that has recently been added to Tranylcypromine and check for accuracy? Fvasconcellos (t·c) 01:05, 8 August 2009 (UTC)

The synthetic route given matches the one in the cited patent, even if the wording isn't that good. I'll rewrite it slightly, but looks accurate to me. Meodipt (talk) 01:15, 8 August 2009 (UTC)

The reaction scheme for the synthesis is inaccurate. The entire synthesis is non-stereoselective (as far as I can see), so there should be no indication of stereochemistry in the reaction scheme. You could put a second diagram to show the resolution of the two isomers at the end (setp 6 in the synthetic description). Physchim62 (talk) 09:41, 8 August 2009 (UTC)

Tranylcypromine Enantiomers

The reaction scheme AND other formulae are still inaccurate. Tranylcypromine is used as a racemate of the trans enantiomers.--Jü (talk) 15:21, 12 August 2009 (UTC)

I've redrawn it to match the synthesis steps. Hope it's OK for everyone.  Ronhjones  ^(Talk) 19:08, 12 August 2009 (UTC)

no it is wrong: the wedged bonds are used to represent trans configuration of phenyl and ester group. Unfortunately there is no way to distinguish the chiral trans isomers from a achiral trans isomer V8rik (talk) 19:15, 12 August 2009 (UTC)

Hi Ronhjones, please complete the nice new synthetic scheme by adding the therm (a) "+ enantiomer" under the last formulae and (b) "four stereoisomers" under each of the intermediates, except the educts. Please explain also in the text. --Jü (talk) 20:04, 12 August 2009 (UTC)

Edited more or less as your suggested.  Ronhjones  ^(Talk) 21:29, 12 August 2009 (UTC)

Conductive polymer

This is my semi-annual plea and prayer for editors to get involved in conductive polymer. These disputes always resolve less acrimoniously with several voices. I dont have time to keep up and will eventually say something that I regret out of frustration. Genius is not required. And the displute is also over a potentially blatant case of conflict of interest and article ownership.--Smokefoot (talk) 13:56, 12 August 2009 (UTC)

ANNINE-6plus

Could someone take a look at this? I get red flags of NPOV (also cleanup would be nice).Headbomb {^ταλκ_{κοντριβς} – WP Physics} 01:48, 13 August 2009 (UTC)

Cypenamine

Probably a mixture of four stereoisomers? May also be a mixture of two isomers or even one of the four stereoisomers. According to the CAS number cypenamine is a mixture of four stereoisomers. Who takes care? --Jü (talk) 09:42, 13 August 2009 (UTC)

Aluminium chlorohydrate

Is one of the structures in PubChem or ChemIDplus correct? --Leyo 06:37, 18 August 2009 (UTC)

Seems unlikely! I'm not sure if the compound has a well defined structure. Physchim62 (talk) 09:30, 18 August 2009 (UTC)

The pubmed and chemidplus structures are total crap (technical term). I looked up "aluminium chlorohydrate" and the related "basic aluminium chloride" in Ullmann's Encyclopedia of Industrial Chem, which usually is pretty decent in terms of formulas and molecularity. The structural description in aluminium chlorohydrate seems pretty good. Al(III) hydroxides are almost always condensed, and the article indicates a keggin or lindqvist structure. The background is laid out in polyoxometalate. The Cl- and OH- ligands are probably disordered and the links between the clusters are probably variable. --Smokefoot (talk) 12:58, 18 August 2009 (UTC)

Just a technical note (I used to work with polyoxometallates in the well-known lab in Paris): aluminium(III) is a bit small to form regular Keggin or Lindqvist structures. I would guess that the "structure" of aluminium chlorhydrate is fundamentally non-crystalline, and that the compound is not particularly well defined. Physchim62 (talk) 15:30, 19 August 2009 (UTC)

Thanks for the explanation. I wonder why these databases just show any structure, even if it is not correct.

It would be quite difficult to draw an appropriate structure I think. :-( --Leyo 13:04, 18 August 2009 (UTC)

My guess is that the simplistic structures shown in bio-databases are generated by robots that require Al to be carbon-like. The deception is a real disservice. But as I have pointed out for years, the structure of chlorophyll in Wikipedia is incorrect because the Mg site is not handled correctly. The list goes on, e.g. calcium gluconate being one I saw recently. We'll eventually get them repaired.--Smokefoot (talk) 13:15, 18 August 2009 (UTC)

I've been searching for a structure for calcium gluconate, but the nearest I could get was calcium galactonate. This differs only in a bit of stereochemistry on the carboxylate side chains, so should be a pretty similar: File:Calcium-galactonate-from-xtal-1996-3D-balls.png.

Ben (talk) 16:29, 18 August 2009 (UTC)

New safety template??

This just appeared under antimony trioxide in a subsection "Summary of human health effect data". Obviously well intentioned, but I could see this kind of table being an invitation to unending additions, often describing non-effects (e.g. "no skin sensitizing") or speculation/extra. We had, I recall, semi-agreed to default to the MSDS, and flesh-out the safety section where the issues are particularly acute (cyanide, etc) or where an environmental threat exists, in which case we would prefer the presentation in paragraph form. So I recommend condensing this new addition into a short paragraph.

Toxicity endpoints	Outcome of the effects assessment
Acute toxicity	ATO has low acute toxicity Oral LD50 rat > 20,000 mg/kg bw Dermal LD50 rabbit > 8,300 mg/kg bw Inhalation LC50 rat > 5,200 mg/m?
Irritation	ATO is skin irritating under conditions that evoke sweating. ATO is not a skin corrosive agent ATO is not irritating to eyes ATO is not irritating to the respiratory system
Sensitisation	Not skin sensitising
Repeated dose toxicity	NOAECinhalation = 0.51 mg/m? NOAELoral = 1,686 mg/kg/day
Mutagenicity	ATO is not genotoxic in vivo after oral administration. No classification is proposed.
Carcinogenicity	ATO induces lung tumours in experimental animals (female rats) at high exposure levels and is therefore classified as carcinogenic category 3 (Xn), R40
Toxicity for reproduction	No concern for reproductive toxicity and thus no quantitative risk characterisation has been performed for fertility and developmental toxicity.

Comments?--Smokefoot (talk) 13:15, 18 August 2009 (UTC)

The table could use some tweaking but I imagine a short paragraph would be awkward & choppy as the toxicological categories are distinct. (I think a bigger issue is that the info should be appropriately sourced with citations from the added references for WP:V — along with reference formatting.) This previous discussion contains reasons why a focus on MSDSs just doesn't make sense, in my opinion. -Shootbamboo (talk) 23:28, 19 August 2009 (UTC)

Seems like we should slap a {{cn}} after every sentence here? --Rifleman 82 (talk) 01:39, 20 August 2009 (UTC)

Almagate

Are sub-stubs composed of only 4 words acceptable in en-WP? --Leyo 21:44, 19 August 2009 (UTC)

If it doesn't meet CSD A1 or A3 and has potential for expansion, there's no real issue. Fvasconcellos (t·c) 20:25, 20 August 2009 (UTC)

BTW: There is a discussion on its structure here. --Leyo 06:32, 21 August 2009 (UTC)

Bromochlorofluoroiodomethane

This article is nominated for deletion on grounds of non-notability; people say it has never even been synthesized. Could someone with access to Scifinder or such check if that's really the case? If there are real references someone perhaps the article can be rescued. --Itub (talk) 17:30, 20 August 2009 (UTC)

A SciFinder search produces no hits on preparation or reactions of this compound. The search turns up 16 papers which all seem to be theoretical in nature (calculation of heat of formation, etc). -- Ed (Edgar181) 17:36, 20 August 2009 (UTC)

Thanks, that was fast! So it is not very notable as a "real" compound, I think. But it may be worth mentioning as "the prototype chiral compound" as I said in the deletion discussion. --Itub (talk) 17:39, 20 August 2009 (UTC)

It's not even that! A reviewer on a paper of mine (for Chemical Communications of all places) wanted me to synthesize enantiomerically pure CHDTI (each of those letters refers to a different atom, it is a strangely chiral form of iodomethane) to prove a point I wished to make… Physchim62 (talk) 19:55, 20 August 2009 (UTC)

Use tritium in the lab? What a great idea... shoy (reactions) 20:57, 20 August 2009 (UTC)

I bet the paper would get glowing reviews. DMacks (talk) 21:05, 20 August 2009 (UTC)

(look for papers that cite doi:10.1021/ja00962a010? There used to be some other refs in one of the WP articles discussing the optical-rotation effects of isotopes in some molecules like that, but the only mention I see right now is of benzyl alcohol α-d. DMacks (talk) 21:17, 20 August 2009 (UTC)

Beilstein Crossfire only gets 2 hits

• Beilstein Registry Number 2202945
• Journal; Papulov et al.; JSTCAM; Journal of Structural Chemistry; 13; 1972; 655,658; 709 (Enthalpy of Formation)
• Journal; Maslov; Maslov; RJPCAR; Russian Journal of Physical Chemistry; 45; 1971; 611 (Other ThermochemicalData)

No hits on the synthesis.  Ronhjones  ^(Talk) 21:56, 20 August 2009 (UTC)

Question

Which is preferred, 2,6-diisopropylphenol or 2,6-di(propan-2-yl)phenol? I'd say the latter, or should it be the trivial? I'm feeling a bit stupid today—the Blue Book wasn't much help. Fvasconcellos (t·c) 20:22, 20 August 2009 (UTC)

IUPAC nomenclature has never been easy for me, but PubChem uses 2,6-di(propan-2-yl)phenol, so you would at least have a source to reference for that name. -- Ed (Edgar181) 12:49, 21 August 2009 (UTC)

ACD/Name generates that as well. I'm changing it in the article. Fvasconcellos (t·c) 13:47, 21 August 2009 (UTC)

Etafedrine

This compound consists of two stereo centers. Thus, four stereoisomers may exist. Is this compound (a) a mixture of four isomers, (b) a mixture of two isomers [which?] or (c) a single isomer [which?]?. Regarding stereochemistry, at this moment, the article is not as precisely as it should and could be. --Jü (talk) 20:50, 21 August 2009 (UTC)

This book shows which isomer is the active one: [8] That doesn't answer the entire question, but should help a bit. --Itub (talk) 21:51, 21 August 2009 (UTC)

There are indeed four stereoisomers, but the pharmacological is one single isomer, the (1R, 2S) isomer. I will change the name on the article page. EdChem (talk) 11:52, 15 September 2009 (UTC)

The chemical structure is not in harmony with the IUPAC name. The IUPAC name is not in harmony with the CAS no. The situation for the different CAS no. looks to me as followes:

• [7681-79-0] mixture of four stereoisomers (this CAS no. is shown in the article)
• [48141-64-6] (1R,2S)-isomer
• [17140-70-4] (1S,2R)-isomer
• [25827-65-5] (1S,2S)-isomer
• [139629-69-3] (1R,2R)-isomer

A pragmatic solution would be to show all four isomers in the box and th revert the name to "mixture of isomers of .....". --Jü (talk) 17:12, 16 September 2009 (UTC)

Colorless solid

Many articles in this project include the phrase "colorless solid", which in context usually seems to mean a white powder. Is there a Wikipedia article anywhere that explains this? --Una Smith (talk) 23:00, 24 August 2009 (UTC)

Request third opinion

To prevent a potential edit war on the article Solid, I am asking the project members to vote here. Thank you. Materialscientist (talk) 01:22, 28 August 2009 (UTC)

Hydroxymethylfurfural page: incorrect picture

Hi there,

I wanted to correct an error on the hydroxymethylfurfural page (http://en.wikipedia.org/wiki/Hydroxymethylfurfural). The picture shown there is incorrect. If you follow the link from the CAS number (67-47-0), and scroll below on that page, you see that the double bond should be an OH group instead.

Regards,

Aloysius Eerhart —Preceding unsigned comment added by Ajjeeerhart (talk • contribs) 10:34, 15 September 2009 (UTC)

Hi, thanks for your comment. In fact, the two structures (the one that is currently on Wikipedia and the one on CAS Common Chemistry) are the same, except that they are mirror images of one another, something which is not important for this molecule. The double bond to oxygen shown on the Wikipedia structure is the same as the "CHO" group shown on CAS Common Chemistry: both denote an aldehyde group, as does the -al ending on the name of the compound. Physchim62 (talk) 11:09, 15 September 2009 (UTC)

Methylhexanamine

Methylhexanamine has two stereocenters. Thus, four stereoisomers may exist: (2S,4S), (2R,4R), (2S,4R), and (2R,4S). Is 4-methyl-2-hexanamine a mixture of all four stereoisomers or just a mixture of (2S,4S) and (2R,4R)? It could be also a mixture of (2S,4R) and (2R,4S) or even a pure (which?) stereoisomer. --Jü (talk) 07:54, 6 September 2009 (UTC)

Paprika oleoresin

Can someone advise me with a problem on names. I noticed that there was no structures on this page, and I was going to do a single drawing of all three items (capsaicin, capsanthin and capsorubin). However when I looked up the structure of capsanthin from the CAS number, I didn't get a structure that seems to agree with the name on the page.

The name on the Paprika oleoresin page for capsanthin is given as (3R,5R,6S,3'R,6'R)-5,6-epoxy-5,6-dihydro-β,ε-carotene-3,3'-diol OR lutein 5,6-epoxide.

The structure I found (Beilstein Crossfire) had names of

• capsanthin
• (all-E,3R,3'S,5'R)-3,3'-dihydroxy-β,κ-caroten-6'-one
• (3R,3'S,5'R)-3,3'-dihydroxy-β,κ-caroten-6'-one
• (3R,3'S,5'R)-3,3'-Dihydroxy-β,κ-carotin-6'-on
• 3,3'-Dihydroxy-β,κ-carotin-6'-on

and an autoname of

• (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

The page name suggests 5 chiral centres - I see only three. The page name also suggests an epoxy - I don't see one. The structure I found agrees with a picture on commons (see thumb).  Ronhjones  ^(Talk) 20:07, 17 September 2009 (UTC)

We seem to have the wrong chemical name op WP for capsanthin. I would go with the one from Beilstein, which agrees with CASRN 465-42-9 and EC-number 207-364-1 (through ESIS), as well as the structure on Commons. It also agrees with a couple of supplier's sites I found. Note that the structure on ESIS doesn't match the name (opposite stereochemistry on one of the hydroxyls), but I'll go with the name. As for the number of chiral centres, well, if you form an epoxide you also form two new chiral centres! But there is no other suggestion I can find that capsanthin actually is an epoxide. Physchim62 (talk) 20:43, 17 September 2009 (UTC)

Problems with uploading pngs

Is anyone else suddenly having trouble uploading png files? Since yesterday sometime it comes up with an error message saying "This file contains HTML or script code that may be erroneously interpreted by a web browser." It has never done that before, I presume its something to do with the software upgrade that was announced on that banner on the main page? Anyway I can upload svgs but prefer not to as they don't display properly in my browser (firefox) so would be good to know why pngs aren't working! Meodipt (talk) 23:47, 17 September 2009 (UTC)

Comment: Please upload chemical structure to Commons and use either PNG or SVG. You have recently uploaded GIF (inappropriate file type) structures to en-WP. --Leyo 12:56, 18 September 2009 (UTC)

Meodipt - SVGs display just fine on all the PCs I use with Firefox - it's just a vector drawing, maybe there is something wrong with your Firefox installation? There's an svg in the thread above this one, that shows just fine (both in FF3 and FF3.5)  Ronhjones  ^(Talk) 19:26, 18 September 2009 (UTC)

I uploaded a PNG to Commons today without any problems: maybe it was just a bug from the software switch. Physchim62 (talk) 20:22, 18 September 2009 (UTC)

Yeah it must have just been a bug as pngs are working again now, and those gifs were only intended as temporary place fillers until I could get the pngs up! I don't think the problem rendering svgs is with firefox but with the svg itself as only some svg images produce the bug, and those that do also do it in internet explorer, and on three different computers I've tried on (hence why I switched exclusively to png in the first place). The problem is to do with the letters not scaling at the same rate as the lines so they look totally out of proportion as shown. Meodipt (talk) 21:57, 18 September 2009 (UTC)

Ok now this is odd, it lets me upload pngs to new pages, but when I went back to replace those gifs one of them worked, but on PF-219,061 it comes up with the same error it did before! Maybe creating the page while they were upgrading the software messed something up? Anyway it would be much appreciated if someone could draw a better image for this page as it seems the only one I can upload that works properly is that crappy gif.Meodipt (talk) 22:12, 18 September 2009 (UTC)

 Done Physchim62 (talk) 22:35, 18 September 2009 (UTC)

Thank you! :-) Meodipt (talk) 22:38, 18 September 2009 (UTC)

I think there is also something odd with svg in the infoboxes. I use Scribus to read in an EPS file and make a SVG file. Now that all works well, but if I set the dimensions of the svg to just fit the drawing, then on display in an infobox it will get stretched - I must use the same dimensions both way (e.g. 200x200). I did read somewhere (this page?) that one can use Inkscape to read in a SVG and then save as a "Plain SVG", which is suppose to work better, but I've not tried that yet.  Ronhjones  ^(Talk) 19:34, 23 September 2009 (UTC)

I've never seen this problem with a PNG I've uploaded and checked myself (I use ChemSketch to make the PNGs). However, every April my students do a poster presentation, and many of them use structures taken of Wikipedia, and I have definitely seen the SVG rendering problem (the PF-219,061 problem shown on left) on several occasions.

One other thing; in IsisDraw, if you change the font size or settings, you may find that when you upload the file somewhere (into MS Word - or presumably into a PNG conversion if it could do that) it reverts to the default settings. For example, you can end up with extra Hs or different fonts appearing in the Word document compared to the Isis file. Meanwhile, ChemSketch I'm not sure if this happens in ChemDraw etc, but could it be your structure drawing package? Walkerma (talk) 19:58, 23 September 2009 (UTC)

I don't have a problem with the intermediate conversion - I use IsisDraw and print to an "Apple Laserwriter 16/600 PS" - except that I don't have an Apple printer, just the driver installed and set to make an EPS file in the driver properties. Scribus is happy to import these EPS files and they look just fine on the screen.  Ronhjones  ^(Talk) 20:59, 23 September 2009 (UTC)

• I am familiar with images that have font size to big: I am using BKchem (Windows) to create svg images. Storing them as plain svg and uploading them to wikipedia will get you the out-of-proportion errors. Storing them as SVG (CAIRO) solves this problem. The wikipedia servers convert svg to png but can only do this in cairo mode. V8rik (talk) 20:11, 23 September 2009 (UTC)

This script might help to improve SVG created with BKchem. --Leyo 22:05, 23 September 2009 (UTC)

BTW: There is a related discussion on Commons: Commons:Commons talk:WikiProject Chemistry#bad font rendering in chemical SVGs. --Leyo 20:17, 24 September 2009 (UTC) If anyone would like to try the new version of ChemBioDraw that offers direct SVG export, there is a fully working trial version (two weeks).

Just tried the new trial version. Judging from the images exported (at right), I reckon it's by far the most convenient way of generating SVG. --Choij (talk) 11:54, 25 September 2009 (UTC)

Yes, they look good. However, I don't like the white background (should be transparent) and that there is no margin. --Leyo 12:21, 3 October 2009 (UTC)

We on the ChemDraw team agree that there should be a margin and the background should be transparent by default. I will file appropriate bugs presently. I do not understand the wish to vectorize fonts mentioned in the linked to discussion. It is my understanding that Wikipedia uses the ACS style sheet settings which recommend very common fonts like Arial which any SVG renderer worth anything should be able to handle. Vectorizing would just bulk up the document.--Glenn Howes 17:33, 5 October 2009 (UTC)

On Wikipedia we do not care that much about the image size, it much more important that the images render reliably, robustly, and future proof, even when using different rendering engines, platforms, and software versions. If that requires vectorized or included fonts, that will definitely be fine for us. Cacycle (talk) 17:58, 5 October 2009 (UTC)

I would appreciate if the user had the choice whether he/she wants to vectorize the fonts or not. --Leyo 07:32, 6 October 2009 (UTC)

Dictionary of chemical formulas/E

Dictionary of chemical formulas/E has been prodded for deletion. 76.66.197.30 (talk) 05:33, 28 September 2009 (UTC)

Amidonitrite

This needs a look from somebody with native speaker capabilities, because it is not 100% chemistry. I cant find it as a compound, but they want to delete it what I would also understand.--Stone (talk)

CFC gap

The article Haloalkane is highly consulted (1412 views/day for Oct. 2009) and is large at 44,455 bytes. CFC redirects to haloalkane. Haloalkane is mostly about CFC-like material but of course haloalkanes are a large class of compounds in their own right. We have no article dedicated to CFC's, but most readers going to haloalkane probably want mainly to read only about CFC's and related compounds such as HCFC's, which also redirects to haloalkane. Freon (5,386 bytes) is modest and only has a history section. Somehow we should address this gap, because the CFC-global warming thing is so topical and we need to give a respectable chemical perspective. We could convert CFC into a self-standing article, but the result would leave out many related compounds, such as CH₂F₂ etc. An alternative approach would be to shift the bulk of the CFC material from haloalkane into halomethane. I am a nonexpert and have no particular insight.--Smokefoot (talk) 03:26, 5 October 2009 (UTC)

good job Smokefoot and anons —Preceding unsigned comment added by 170.170.59.138 (talk) 22:02, 10 November 2009 (UTC)

2-Diphenylmethylpyrrolidine / stereochemical desaster

(a) In the Box no stereoinformation in the formulae is given, (b) According to the IUPAC name, die configuration is (R), (c) Acording to the text the configuration is (RS) = (±) = racemate, (d) According to 2 out of 3 formulae in the reaction scheme the configutation is (S), (e) surprisingly no configuration is given for the CBS reagent. --Jü (talk) 11:23, 25 October 2009 (UTC)

Sodium azide

The articel on Sodium azide contains a large section a single intoxication event in a University. We should change that to a better form, because a lot of people have died of azide poisoning in the time since it was discovered.--Stone (talk) 20:01, 27 October 2009 (UTC)

Raney nickel

I have concerns that Raney nickel may no longer be a featured article. See further information here. Does anyone want to help fix it up or list it at WP:FAR? Ten Pound Hammer, his otters and a clue-bat • ^{(Many otters • One bat • One hammer)} 02:04, 7 November 2009 (UTC)

There are a few issues with that article, but I believe they all can be quickly fixed. Started that. Anyone willing to join is welcome. Materialscientist (talk) 02:43, 7 November 2009 (UTC)

Dihydroxyalumanous acid

Editors might want to ponder the ongoing efforts by User:Plasmic Physics to include some pretty strange IUPAC nomenclature. My suggestion is that he put the really weird names into the disappearing IUPAC slot on the ChemBox vs the lead. But the user is generally unresponsive. Possibly someone with administrative influence could induce this user to discuss plans and accept some sort of consensus-driven guidance.--Smokefoot (talk) 13:57, 20 November 2009 (UTC)

I have reverted some of his edits, and will contact the user. However, it would be useful to have a more specific discussion (with links) on his name changes and where we don't agree. I can see that some names are not practical and not used, but it is not always evident (to me). Having IUPAC behind ones back may be considered as an argument. Materialscientist (talk) 01:04, 21 November 2009 (UTC)

Chemical-family trees

Aushulz told me about this fabulous technique for showing chemical lineage: Template:Familytree from it.wikipedia. Here is one for ethylene usage here and acetic acid's parentage and uses here. This display method could prove really useful for showing readers how molecules connect together. --Smokefoot (talk) 00:54, 24 November 2009 (UTC)

Ammoinum fluorosilicate

I have started on an article for ammonium fluorosilicate (a.k.a. hexafluorosilicate), a salt of fluorosilicic acid. I hope someone can add more properties. It is important in discussing bararite and cryptohalite. Johnny Mineralogist (talk) 03:09, 24 November 2009 (UTC)

What about ChemIDplus? --Leyo 11:34, 24 November 2009 (UTC)

There are some pictures of the unit cell of the hexagonal modification at Commons:Category:Diammonium hexafluorosilicate.

Ben (talk) 14:46, 24 November 2009 (UTC)

Talk:Trinitrotoluene

Discussion here, which may be of interest to WikiChemists. --Rifleman 82 (talk) 17:53, 26 November 2009 (UTC)

Methiodide

Hello, I looked for methiodide in wikipedia I found nothing, but it was instead in wiktionary, and that happens all the time! I know that a dictionary and an encyclopedia are different, but I think that this distinction is so pedantic it is farsically pathetic! (PS. Despite my complaint, I think wikipedia editors are doing a lot for the world). PhD student, KCL —Preceding unsigned comment added by 159.92.90.128 (talk) 11:52, 27 November 2009 (UTC)

OK, I have created methiodide with some basic information. The definition at Wiktionary appears to either be incorrect or is missing its more common meaning as a quaternary ammonium salt. -- Ed (Edgar181) 15:33, 3 December 2009 (UTC)

Protonation of monosodium glutamate

I believe some time back, we agreed to adopt the "neutral" form, as opposed to the zwitterionic form for amino acids. That aside, shouldn't the side chain of glutamic acid be more acidic? Perhaps the image needs updating. --Rifleman 82 (talk) 16:20, 3 December 2009 (UTC)

Wikipedia:WikiProject Chemicals/Organization, sacred cow?

Recent edits to this list were reverted. On whose authority? I have long felt that the list was a good start, but that like all drafts, probably would benefit from being revised. Of course, I have only great respect for the spirit of the list, but its just a list... And no one is really the boss here, are they? So my suggestion is that we figure out some orderly mechanism for editing it. P.S. Holmium oxide is important - sez who?--Smokefoot (talk) 19:12, 3 December 2009 (UTC)

On Holmium(III) oxide - chemicals with more developed articles might seem more important, which is not (that article was expanded for DYK). It has some uses, but more on the exotic side. Materialscientist (talk) 00:49, 4 December 2009 (UTC)

Perhaps it was an attempt to have a representative compound from every element? --Rifleman 82 (talk) 01:27, 4 December 2009 (UTC)

Yes, the list is a sacred cow. This worklist was created over five years ago to cover all 'important' articles in WP:CHEMS on various chemical fields, e.g., the inorganics, the organics, the polymers, the commodities, etc. It was devised before things such as categories were used for a similar purpose, and before bots were able to do assessment gathering. Actually, the assessments as currently done in WP are based on the assessment in exactly this list. Therefore IMHO it should be preserved for posterity as a sacred list. Is there some sort of Archived status in WP, in which the list is accessible for people to see it, but not edited anymore? Then that is what I would recommend for its status. Wim van Dorst (talk) 00:37, 12 December 2009 (UTC).

We can add a {{historical}} tag, and protect the page? --Rifleman 82 (talk) 01:39, 12 December 2009 (UTC)

That's it, Rifleman! This is of course my personal opinion. Should we vote about this or so, or not? Wim van Dorst (talk) 20:57, 12 December 2009 (UTC).

I'd like to know if anyone is actually using the worklist anymore. I'm not, and I haven't done so for a couple of years now. If it is still useful, then it should be active and should be edited. If it is no longer used – as I think is the case, and as Wim seems to tacitly accept – then it should be archived, and the "core" category disabled from the {{chemicals}} banner.

I think the list is of historical interest. It was an organized way of of trying to improve our coverage of chemical compounds. That it has become superceded is obvious by its length – about 300 articles, when we now have more than 5000 articles on chemical compounds. It also nicely illustrates one problems that chemical editors have: it is easy to start an article about a compound, but do we actually have anything to say about it? I tend to call this the radium chloride problem, and if anyone can find more to say about the most important compound of radium they are welcome to edit that article (I spent several afternoons in the university library looking fo info, but couldn't find much).

If we have a "worklist" at the moment, it is surely the CAS Common Chemistry set. With one or two exceptions (mostly elements), substances on the Common Chemistry site have more than 1000 published references that cite them, so we should be able to find something to say about them! To reply to Smokefoot, Ho₂O₃ is listed at Common Chemistry, so it is not just Wikipedia who says it's important. Physchim62 (talk) 01:05, 13 December 2009 (UTC)

I stand corrected, I will bear in mind that holmium oxide is important, smirk. The "sacred cow list' was indeed influential at one time. Now back to the present, where is this common chemicals list? I see the searchable site but we want the list.--Smokefoot (talk) 17:32, 13 December 2009 (UTC)

For the WP:CHEMS wikiproject, we created a list with the top 50 chemicals in some six groups of chemicals, and WP:CHEMS's target is to improve these 285 articles to A-Class. Now there are two things under discussion:

1. the "Organization" projectpage (worklist): In 2005 we used the project page " Organization" for listing our worklist, simply because no alternatives were available. Nowadays, we have a category for that, which is automatically scanned for progress. So, yes to making the page {{historical}}, but don't remove the 'core' from the project template, as the related category is still in use as the current worklist.
2. A target list of articles to work on (worklist). Do we need another target? Don't think so. We haven't even finished the old one yet. Wim van Dorst (talk) 21:40, 13 December 2009 (UTC).

Yes, Rifleman is right - the idea was to ensure that every non-radioactive element in the periodic table was represented, just as part of a broader set. If you look at the list it's not supposed to be the 287 most important, but it's supposed to ensure that no area of chemistry is ignored, and we get decent coverage across the spectrum of compounds. Before we started considering the collection more broadly, most chemical articles were either on aromatic organics or on hallucinogenic drugs, which happened to be what people wrote on. Many were also very popular pages - but then again, these things feed themselves (in 2004, drug people looked on WP for info, but chemists typically didn't). Once we got a broader base of articles, I think it helped draw in new readers because chemists found their own field represented. With the lanthanides, many of the compounds picked were chlorides, but some were oxides - these are the most common. Even the Ho2O3 article gets around 10 hits a day, and gold(III) chloride gets over 100 a day, and .

Our project goals are still aligned to bringing this list of compounds up to A-Class. Do we still want to do this? If not, what are our new goals? If they are still valid, can we use the bot to generate a report for us, so we can track progress automatically? (The new 1.0 bot is being beta tested and should be much more flexible & customisable in that sort of way, I think). Sorry I'm just so busy right now in "real life" or I'd work on this more myself! Walkerma (talk) 18:38, 21 December 2009 (UTC)

Martin, the bot has been tracking progress of WP:CHEMS already a long time. That's the main reason why the Organization page went in disuse. And most of us are probably as busy as you, which is indeed a pity because progress is limited. Yet, as you can see in the long term statistics in section 1 above, there is a continued progress. so, all, keep up the good work! Wim van Dorst (talk) 22:03, 22 December 2009 (UTC).

AFD Dielectric relaxation as a chemical rate process

Wikipedia:Articles_for_deletion/Dielectric_relaxation_as_a_chemical_rate_process - just to bring for your attention. Materialscientist (talk) 06:51, 6 December 2009 (UTC)

Checking needed

Would someone please check this edit at Phenol, and this edit at tert-Butanol, and the new article (Nitrocarboxylic acid) created by the same editor. The edits are not wrong, but seem unwarranted to my amateur eye. Johnuniq (talk) 07:31, 14 December 2009 (UTC)

Phenol & t-butanol are reasonable. The new article doesn't say much. --Rifleman 82 (talk) 14:35, 14 December 2009 (UTC)

I looked for something to write about Nitrocarboxylic acid, but couldn't find anything for this general class of chemicals. PROD'ed. DMacks (talk) 19:59, 14 December 2009 (UTC)

I recommend conversion of nitrocarboxylic acid to a redirect of some sort or deletion. Yes, there are nitrocarboxylic acids and lots of other binary combinations, but the class does not seem noteworthy.

Templates related to opium poppy derivatives

There is a proposal on WP:RM to move (rename) Template:Components of Opium. I think it could do with an overhaul, and perhaps a merge with Template:Opioids. Any takers? Discussion of the move proposal is on Template talk:Components of Opium. --Una Smith (talk) 21:42, 20 December 2009 (UTC)

Third opinion on Copper indium gallium selenide

There is a minor edit warring, between myself and IP:59.120.72.94 later registered as user:Ccurpenny, at Copper indium gallium selenide (see page history) about whether or not to include a list of companies producing working with CIGS/CIS cells. The question is more general than this article, thus please express your opinion.

• I believe the list should be moved to the List of photovoltaics companies. This article is about chemical compound, not about manufacturers. Materialscientist (talk) 05:21, 21 December 2009 (UTC)
• The link to the list seems more appropriate to me than listing the individual companies in the article. If there is one or a small number of companies whose names are most associated with this technology, than they can be mentioned in the article (with appropriate sourcing, of course), but I see no need to list a dozen+ in the article without any explanation. Yilloslime ^T_C 05:49, 21 December 2009 (UTC)
• We've had this sort of discussion before, and the consensus has been not to include suppliers or manufacturers. The exception is where a compound is particularly associated with one or two companies, for example if it is proprietary technology or if it is usually known by a trade name (eg Proton Sponge). Physchim62 (talk) 07:41, 21 December 2009 (UTC)
• Added a new page List of CIGS companies, will add to CIGS WP page when it's able to edit. -Ccurpenny —Preceding unsigned comment added by Ccurpenny (talk • contribs) 02:53, 22 December 2009 (UTC)

  Added a link to that page into Copper indium gallium selenide. Materialscientist (talk) 03:04, 22 December 2009 (UTC)