Wikipedia talk:WikiProject Chemicals

The discussion here concerns all parts of the Chemicals WikiProject, including the infoboxes, lists, standards, includes/excludes, tools, contributors, etc etc etc. Feel free to add your comments to any section here, or start a new topic. Older and closed discussions have been archived (2005, 2006, 2007, 2008). Topics not specifically related to the Chemicals WikiProject would be better served at other wikipages.

Status statistics

WPChem worklist pages by quality Quality Total FA 2 GA 16 B 172 C 76 Start 110 Stub 14 List 1 NA 4 Assessed 395 Total 395 WikiWork factors (?) ω = 1,486 Ω = 3.81

The worklist shows the actual work to be done to achieve the goals of the Chemicals wikiproject. The choice of important compounds articles to work on has been finalized in an earlier stage of the wikiproject (around mid 2005), and no further articles are added, although we remain open for strong suggestions on this talkpage. The work these days focuses on improving the articles, from Chem Stub all the way to Chem A-Class articles. The table below shows that progress.

Worklist historical status
	2005			2006				2007				2008
Grade	Jun	Jul	Oct	Jan	May	Jul	Oct	Mar	Jun	Oct	Dec	Feb	May	Aug	Dec
Template:Chem FA	2	2	2	3	4	4	4	6	6	6	7	7	7	7	7
Template:Chem A-Class	27	29	24	25	28	28	28	27	23	19	18	18	17	16	15
Template:Chem B-Class	71	70	84	87	101	121	130	148	153	156	157	158	179	180	182
Template:Chem Start	112	106	131	178	199	197	190	174	174	174	181	180	150	153	158
Template:Chem Stub	97	106	130	82	46	32	29	27	26	27	19	19	29	26	20
unclassified	76	59	nil	nil	nil	nil	nil	-	-	-	-	-	-	-	nil
Total	385	372	371	375	378	382	381	382	382	382	382	382	382	382	382
percentage ≥Chem Start	55.1	55.6	65.0	78.1	87.8	91.6	92.3	92.9	93.1	92.9	95.0	95.0	92.4	94.0	94.8
weighted progress, %	42.2	43.8	50.4	54.1	57.8	60.0	60.8	62.2	62.1	61.7	62.3	62.4	63.0	63.1	63.5

The percentage ≥ Chem Start was indicative of the initial effort. Now that we are progressing to more advanced progress, the weighted progress indicator is used, calculated as (Unclass*0 + Stub*1 + Start*2 + B-Class*3 + A-Class*4 + FA*4) / (Articles*4). We are aiming for A-Class, and humbly not for FA.

Chemicals articles by quality and importance Quality Importance Top High Mid Low NA ??? Total FA 1 2 2 2 7 FL 1 1 GA 1 12 21 12 46 B 21 138 326 275 12 772 C 7 74 364 1,172 26 1,643 Start 96 1,141 5,285 134 6,656 Stub 340 10,333 2 147 10,822 List 2 8 1,562 53 334 1,959 Disambig 3 30 33 Template 383 383 NA 16 170 3,542 3,728 Other 1 17 18 Assessed 30 324 2,218 18,816 4,027 653 26,068 Unassessed 1 14 176 191 Total 30 324 2,218 18,817 4,041 829 26,259 WikiWork factors (?) ω = 107,197 Ω = 5.37

Statistics for all chemicals, as registered by the bot, also see complete list

TfD nomination of Template:Fchm

Template:Fchm has been nominated for deletion. You are invited to comment on the discussion at the template's entry on the Templates for Deletion page. Thank you.Rifleman 82 (talk) 04:07, 5 October 2008 (UTC)

Monsieur Frémy

I ran into an article that says that KHF₂ is known as "Frémy's salt", but there is another Frémy's salt - a stable radical anion. Apparently, he decomposed KHF₂ to make for the first time HF. Those looking for a project of willing to offer advice:

• We dont yet have an article on KHF₂, which is semi-important industrially. I was thinking of moving bifluoride to KHF₂ - is that a bad idea? Maybe we should have an article on the anion and a separate one on the salt.
• Has anyone heard if there two Frémy's salts?
• Our HF articles - Hydrofluoric acid and Hydrogen fluoride - don't mention its discovery, which seems like an oversight.

--Smokefoot (talk) 18:28, 5 October 2008 (UTC)

I'd never heard of any Frémy's salt until half-an-hour ago! But the one we have an article on is certainly called that. Hydrofluoric acid was being used to etch glass in the 17th century, according to Greenwood and Earnshaw, and was also prepared by Scheele. French Wikipedia credits Frémy with being the first to prepare anhydrous HF, which sounds reasonable–he certainly did work on fluorine chemistry. The bifluoride anion is a nice example of divalent hydrogen, so we might want a seperate article on KHF2. Physchim62 (talk) 20:10, 5 October 2008 (UTC)

I would prefer having a separate article for the anion itself, which can discuss general issues such as bonding and solvation, and specific articles on each notable salt. Note that we already have one on ammonium bifluoride. --Itub (talk) 08:49, 6 October 2008 (UTC)

Articles with no talk pages

Many articles of interest to this wikiproject have no associated talk pages, and as a result are not categorized as "belonging" to the wikiproject. I decided to do an experiment and produced a list of all the articles in Category:Inorganic compounds and all its subcategories, recursively (excluding a few "non-chemical" categories, because otherwise we end up including skiing categories!). There were 1850 articles in the resulting category tree, out of which 248 have no talk page. I listed these 248 missing talk pages at User:Itub/Inorganic compounds without talk pages. These should be useful if anyone wants to look at those articles and rate them or just add the wikiproject template. Of course, there are many false positives, or articles that are better classified under "chemistry" or "minerals" rather than "chemicals". And there are also "false negatives" because there can be articles that do have a talk page but do not have the wikiproject template.

If anyone is interested, I also posted the category tree at User:Itub/Inorganic compound category tree. These lists are semi-automatically generated so I can produce other lists. The problem is that the lists can be unmanageably large unless I add lots of categories to the "blacklist" (for example, the list for organic compounds ends up including tens of thousands of articles on proteins and enzymes!). --Itub (talk) 16:54, 6 October 2008 (UTC)

Thanks, that's very helpful! Walkerma (talk) 01:36, 7 October 2008 (UTC)

A trick to get a good list is to get everything transcluding a {{chembox}} or {{chembox new}}, putting 'Talk:' in front of all of them, and run that list through AWB. If it does not contain a {{Chemicals|parameters}}, add one with empty parameters. Maybe something for chem-awb? --Dirk Beetstra ^{T C} 15:28, 7 October 2008 (UTC)

That is true, but I wanted to try to catch the articles with no chemboxes too (not uncommon for stubs). I wanted something that can also help find WikiProject Chemistry articles, and those don't have infoboxes. --Itub (talk) 15:34, 7 October 2008 (UTC)

Actually, I've done that before, around 27 June. Of course, I'm happy to do it again, but we shouldn't pretend it's perfect, like Itub says. --Rifleman 82 (talk) 17:46, 7 October 2008 (UTC)

Chembox news

Just to let people know that {{chembox}} is now fully equivalent to {{chembox new}}, and so editors can (and should) now tag articles with {{chembox}}. The old chembox is currently at {{chembox old}} (logically!). Starting from today, I (and hopefully a few others [hint]) will be changing the template on existing articles, slowly at first to catch any possible bugs in the interface with CheMoBot, then hopefully finishing with a bot run. Physchim62 (talk) 12:40, 7 October 2008 (UTC)

What would be really great would be if those updates included the curated data from the SDF file (hint!). Thanks a lot for this upgrade, PC. Walkerma (talk) 13:13, 7 October 2008 (UTC)

Chembox property count

See User:Itub/Chembox property count. It is a list of how many chemboxes provide a given property, obtained after parsing 4475 infoboxes, plus a few extra tables. This is helpful for finding certain errors in infoboxes, such as typos in the parameter names, and for things like seeing how many pKa's we have available. I have all the data loaded up into a SQLite database (3 MB), in case anyone is interested. The parsing is not perfect, but appears to be mostly functional. With the database it is easy to produce a table for a given property, such as a table of pKa's. --Itub (talk) 12:34, 8 October 2008 (UTC)

I took a whack at fixing some User:Itub/Chembox property count#Properties used by only one chembox...removed if, added comments for where I got stuck. DMacks (talk) 02:16, 22 October 2008 (UTC)

Best Practices for skeletal images

From Talk:Caffeine#Is the image of the Caffeine Molecule correct? (among other places), lay-readers can understandably get confused by "all the missing atoms" in standard skeletal diagrams. It would be helpful if the image description had a link to skeletal formula so anyone who cared to read about the image could learn what the heck it meant. DMacks (talk) 02:00, 22 October 2008 (UTC)

Personally, I think that we overuse skeletal images - professional chemists are comfortable with them, but a page like acetone is more likely to be read by an undergraduate or A-level student, and some of them will be baffled by the strange lines in the structure page. A link to the skeletal formula article is a good idea with more complex cases, but an unnecessary complication for simple molecules. I think a skeletal formula is fine for drawing oleic acid or bleomycin, but it's inappropriate as the only representation for something very common with only two or three carbons. Walkerma (talk) 15:59, 28 October 2008 (UTC)

Flagging validated/curated data in chemboxes for users

We are currently uploading validated and curated data into chemboxes (see Wikipedia:WikiProject Chemicals/Chembox validation). However, there is no way for a random user to distinguish whether a CAS number was supplied by CAS, or typed in by someone's pet monkey. So we would like to clarify this for users, and we've tested out a parameter that indicates data as validated, and if the entry is edited at all the "validated" flag disappears. You can see an example here, where the CAS# is one supplied by CAS - so in fact we already have a working method that could be implemented. It relies on Beetstra's bot, which defines a particular version from an article history as the source of the validated data.

We were thinking of a color-coded scheme, something along the lines of:

• Green/bold => Validated against a reliable source (i.e., as reliable as it can get)
• Yellow => Checked by a WP:Chem member
• Black => Unchecked
• Red => Recently edited, needs checking

Although a link would be needed to explain what the codes mean, we have to assume that most users wouldn't click on that, and so having something that is intuitive (most people associate green=good, red=bad) would flag it sufficiently even for a user who didn't click for a definition. The exact details could be debated.

I could have posted this at the ChemBox discussion area, but this seems to have broad implications - AFAIK, this could be the first place on Wikipedia where validated content is flagged as such - so I thought we should raise it here, where many more people are likely to see it. So, does anyone have any comments on how best to do this? Cheers, Walkerma (talk) 16:13, 28 October 2008 (UTC)

Just a general comment: In de-WP, we declared it compulsory to use ref tags for all non-trivial parameters in the chemboxes (see e.g. Methan). The CAS number is treated as a trivial parameter that does not need to have a reference, but it can normally be checked in one the references for other properties. What you intend to do here seems to be similar to a certain extent to what is proposed as quality versions. :-) --Leyo 17:50, 28 October 2008 (UTC)

I like Green Bold as shown to indicate the reliable source. Yellow to red etc makes sense to me also. The Black vs red makes less sense. I would leave three levels of red, yellow, green. Red by default should mean unchecked in my view.--68.33.211.217 (talk) 20:12, 29 October 2008 (UTC)

I don't like red for the last stage: it would be confused with redlinks. Let's keep it at a three-level scheme for the time being, if need be we can expand it later. Physchim62 (talk) 21:02, 29 October 2008 (UTC)

OK, let's meet on IRC tomorrow and (hopefully) we can implement this starting tomorrow. We need to start using it as we add validated data in the coming weeks. If you can't make it, please leave any comments here. Walkerma (talk) 02:02, 11 November 2008 (UTC)

Three-level is easy. "If the ref-field matches one of certain known values (CAS for cas#, certain datafile notations for SMILES, etc.) do fmt1, otherwise if it's not blank (i.e., has some unknown value) do fmt2, otherwise (i.e., no ref-field value) do fmt2". Because each field has its own formatting template, each can recognize appropriate "known" refs and include or not an actual footnote or other ref text (to balance clutter vs verifiability and "trivial/obvious", etc. DMacks (talk) 02:10, 11 November 2008 (UTC)

...and now implemented for CAS#s. Consider Boric acid:

• not-quite-reliable source
• authoritative or other known-good source
• unverified

DMacks (talk) 15:39, 11 November 2008 (UTC)

Yellow is pretty much invisible... although that can be a good thing if it's used to flag unreliable data? :) Fvasconcellos (t·c) 16:16, 11 November 2008 (UTC)

Yes, we're discussing it on IRC now. I think dmacks has already changed it - do a refresh! Join us if you can, Walkerma (talk) 16:24, 11 November 2008 (UTC)

The formatting action happens in {{chembox val fmt}} DMacks (talk) 16:54, 11 November 2008 (UTC)

"Join us if you can"

Oops...

The new color looks much better. When (and how) does this start to roll out? I'll start uploading the last set of validated data (401—500) tomorrow, by the way. Fvasconcellos (t·c) 00:42, 12 November 2008 (UTC)

Actually, I see Martin has claimed those entries. Should I work on 100–200 instead? Fvasconcellos (t·c) 00:47, 12 November 2008 (UTC)

The new system is now enabled, so you can start using it straight away! Remember, only use green for the CAS-validated CAS#s for now. Yes, why don't you take 100-200. I will get onto 400+ once the 1.0 work dies down. Our article selection is now complete (an immense task) now I'm on the indexes. Antony should have a new set for us in a fortnight or so. Walkerma (talk) 04:50, 12 November 2008 (UTC)

• Its probably a good thing. I see some good results, e.g., in boric acid. But not being in on the development, can anyone please point out how it works? Wim van Dorst (talk) 21:06, 12 November 2008 (UTC).

Sodium fluoride under attack again

I ask that others help with controlling the antifluoridation enthusiasts on sodium fluoride. This additive elicits intense feelings from some readers. Wikipedia has set up Opposition to water fluoridation, fluoride poisoning, fluorosis, Dental fluorosis, skeletal fluorosis, and probably some others sites to allow the antifluoridation groups to expound their views at some length. So please lend a hand, especially experienced editors.--Smokefoot (talk) 00:37, 1 November 2008 (UTC)

It seems that issue has self-destructed in a big way, thanks to some intervention from others. I've added what is (hopefully) some basic info into the article, not to appease the anti-fluoride-masses but just to bring into line with similar compounds' pages. I know we're trying to steer away from "How-to" etc and towards MSDSs, but is there a standard "Safety" format that we could follow? Freestyle-69 (talk) 02:03, 3 November 2008 (UTC)

That definitely qualifies as a melt-down. We iodize salt, chlorinate water, hydrogenate food, and inject unconscious patients with iron cyanides, but for some reason a segment of society has really latched on to the water fluoridation thing.--Smokefoot (talk) 02:26, 3 November 2008 (UTC)

Benzyl alcohol

It would be greatly appreciated if someone could have a look at the edits here from the last day or so, since its redirection from Phenyl methanol [1]; I initially reverted some unsourced changes, and would like to know what is the proper nomenclature. JNW (talk) 19:08, 1 November 2008 (UTC)

• According to IUPAC rule A-13.1, I'd say it should be called phenylmethanol. Wim van Dorst (talk) 20:47, 1 November 2008 (UTC).

Do you suggest reversing the redirection? If so, I'd prefer that someone with a better understanding of chemistry than I possess do the honors. JNW (talk) 21:06, 1 November 2008 (UTC)

• Let's give it a few days: others can contribute here too. And then the discussion whether the article should be named phenylmethanol which is less used than benzyl alcohol is a different topic. Wim van Dorst (talk) 22:09, 1 November 2008 (UTC).

Great. Thanks. JNW (talk) 22:14, 1 November 2008 (UTC)

Google data for discussion:

• "benzyl alcohol" - 1,490,000 hits

• "phenylmethanol" - 9,330 hits

Ratio "benzyl alcohol" : "phenylmethanol" = 160:1.

Ben (talk) 19:06, 2 November 2008 (UTC)

Thanks, Ben: thought so. That means that the article should be benzyl alcohol, but the IUPAC name in the chembox should be phenylmethanol. Most important for me personally is consistent use of the name throughout the article, though. Wim van Dorst (talk) 22:34, 2 November 2008 (UTC).

sodium silicate (aka sodium metasilicate)

The structure picture in the chembox is incorrect - I have tried to remove it but its still there. I think it needs a fresh pair of eyes! Can someone take a look at this please.--Axiosaurus (talk) 18:23, 2 November 2008 (UTC)

Why don't you upload a new image in place of this one at commons? (I've deleted the local copy, and it no longer displays automagically). Or, describe it to me and I'll do one up? --Rifleman 82 (talk) 02:18, 3 November 2008 (UTC)

Well the one shown is definitely incorrect, but is there one correct image? I guess that there must be materials of the formula Na₄SiO₄ and Na₂SiO₃, but sodium silicate solutions are probably complex mixtures of oligomers, with varying degrees of protonation. My guess is that the ²⁹Si NMR people have the info. I am no expert, but that's my guess.--Smokefoot (talk) 02:39, 3 November 2008 (UTC)

Crystal structure of Na₂SiO₃: W. S. McDonald and D. W. J. Cruickshank, Acta Cryst. (1967). 22, 37-43. I can make a 3D image if appropriate.

Ben (talk) 10:32, 3 November 2008 (UTC)

Hey Ben, just commented to Axio on my talk that you're probably the best guy for the job - you're the expert for crystal structures. Hope you can help! --Rifleman 82 (talk) 17:26, 3 November 2008 (UTC)

The whole "toxic chemical" thing

Partially in reference to the sodium fluoride issue (above), but as a general concern and question:

As most if not all of us know, pretty well anything will kill us if we ingest/inhale/whatever enough of it. We're scientists, or at least educated in this area, so we know that dose X of jiggazantium will cure our somethingitis, but dose X x 100 will give us 3 legs and a bad case of death. But the masses... in general they read the latest news story, or hear something from a friend (both of which we know are great sources...), and start making their own conclusions. Based on the evidence that they have, they make a pretty reasonable decision and decide that since melamine is toxic, we now shouldn't eat off our kitchen benches. I've found that non-scientists are pretty quick to read the first thing and take that as gospel- everyone's too busy to actually find out more for themselves.

I feel that as editors we're tasked with providing a balanced perspective on topics, but when an MSDS for something says it's toxic, we obviously can't say that it's harmless, even if it's therapuetic/beneficial in low doses. The masses won't generally look at an LD₅₀, as they wouldn't be expected to understand that sort of thing. The average Joe wouldn't read an MSDS (or maybe even know what it is), esp if it's only linked from the chembox. But, I get the idea that WP is the first place that people will go to to check these "nasty chemicals" out. Flattering, but onerous.

So, my question is- could there be some standard form of statement/wording that can be included in the "Safety" (or similar) section to "dilute" or further explain the apparent toxicity of so many compounds that people are exposed to? And for that matter, explain that too much of even the good things will do the reverse? Freestyle-69 (talk) 03:02, 3 November 2008 (UTC) Sorry for a potential can of worms

This toxicity issue is indeed one of the hugest cans of worms. My nearly universal recommendation: we refer to the MSDS, which is more authoritative than we can ever hope to be. In doing so, we dissociate Wikipedia from giving advice (Wikipedia:What Wikipedia is not). When the toxicity is notable, we create articles dedicated to the toxicity, such as cyanide poisoning. In some cases, the toxicity is controversial,, and we create water fluoridation controversy. In yet other cases, the toxicity is chemically instructive, phosgene comes to mind, in which case we discuss the mechanism briefly in the safety section. So my vote is to defer to the MSDS and avoid offering more than a few words. And we cannot be too absolutist, of course. I look forward to hearing other's views.--Smokefoot (talk) 03:25, 3 November 2008 (UTC)

The MSDS, if anything, will scare the average non-scientist even more than necessary. MSDS are generally overly paranoid IMHO, maybe because they are usually provided by the manufacturer and the manufacturer doesn't want a lawsuit, but that's just a guess. Just look at an MSDS for sodium chloride (I'm looking at the Sigma-Aldrich MSDS, but I couldn't find a URL to link to). It "may" be harmful in a number of ways, you need glasses and gloves to handle it, should consider a self-contained breathing apparatus in case of fire, and people inhaling it may need artificial respiration. I guess one can never be too careful, but this looks almost like it was taken from http://www.dhmo.org . --Itub (talk) 06:52, 3 November 2008 (UTC)

An MSDS for sodium chloride. I rather liked "Chronic Exposure: No information found." Surely it should say "causes high blood pressure and strokes", or something similar. ;-) Iain99^{Balderdash and piffle} 23:32, 3 November 2008 (UTC)

Now, my suggestion is the following. Although a link to an MSDS can be useful somewhere, it is better to link to something more scientific. Give the LD50, but put it into perspective by comparing it with well-known substances, both "toxic" and "nontoxic". For example, people might be less scared if they knew that the LD50 of melamin is actually higher than that of sodium chloride! And yes, children have died from sodium chloride poisoning too. My guess is that large amounts of melamin probably don't taste as bad as large amounts of NaCl, and that is what can make it more dangerous. --Itub (talk) 06:56, 3 November 2008 (UTC)

Don't forget that more people die from inhalation of water that from inhalation of any other chemical (except possibly dioxygen). Physchim62 (talk) 23:02, 3 November 2008 (UTC)

I agree MSDS's can be inadequate/overdone/silly. For the bigger picture, I wager most people looking up chemicals on WP to get an idea of "toxicicty" are curious about low levels of exposure, like this data: phthalates have been linked to smaller penis size.[2] Different biological effects are thought to occur from different low level chemical exposures. In general, MSDS's are written for use in concentrated form by workers. I think we should accept a perspective of openness towards including data about toxicity, instead of attempting to fight or marginalize that information. The dirty "c" word comes to mind otherwise...censorship. -Shootbamboo (talk) 03:26, 24 December 2008 (UTC)

Fluorenol

Could someone start an article for Fluorenol (hydroxyfluorene)? Perhaps it has another name, in which case a redirect should be created. Fuzzform (talk) 00:11, 5 November 2008 (UTC)

Also, why on earth does it have that name, since it has no fluorine in it? (PubChem 74318) Fuzzform (talk) 00:18, 5 November 2008 (UTC)

See fluorene. --Rifleman 82 (talk) 03:31, 5 November 2008 (UTC)

I started the article as a stub with some basic physical properties, I'll try to add some text to it shortly. -- Ed (Edgar181) 14:17, 5 November 2008 (UTC)

Approved

User:CheMoBot has been approved this morning, and from now on it is saving logs 'below' Wikipedia:WikiProject Chemicals/Log and Wikipedia:WikiProject Chemicals/Log_2 (see Wikipedia:WikiProject Chemicals/Log/2008-11-11). I am a bit tweaking with it now. The logs are a bit long at the moment, but it is easy to hide parts by adapting the Logline template (User:CheMoBot/Logline), I think everything with a 'level' of 0 can be hidden in the logs.

I will be busy tweaking this all in the next days, please let me know if there are things which should be different. @Admin-template-programmers, it would be nice if I could get some help with User:CheMoBot/Logline, fancy that up a bit. --Dirk Beetstra ^{T C} 12:25, 11 November 2008 (UTC)

I have hidden the 'level=0' messages now (which hides some of this morning which actually got a wrong level assigned) through a change in the template. This hides all edits which are not changing values in the box and are not adding an external link (but the data is still there in the edit mode on the page). Please keep an eye on the hidden ones, if there are ones mistakenly hidden that may be due to a mistake in the bot. --Dirk Beetstra ^{T C} 14:57, 11 November 2008 (UTC)

Francium hydroxide

Francium hydroxide was WP:PRODded by someone. 76.66.195.63 (talk) 06:43, 26 November 2008 (UTC)

I prodded it, together with francium fluoride. These are just speculative, unreferenced stubs on nearly unknown compounds. Although there is some published information in Russian journals from the 1960s and 1970s (that I don't have access to), I very much doubt that it will be enough to justify separate articles. If someone can dig up those journals (and can read Russian, presumably), then the information can be added to the francium article. Funny story: when I was searching for these papers I found some patents for inventions that supposedly can use francium fluoride. They said something like: "or any other alkali metal halide, including ... francium fluoride". As you may know, chemical patents are sometimes a bit broad in their claims... --Itub (talk) 06:53, 26 November 2008 (UTC)

I had a look a while back as well, when francium was up for FA, and found even less than Itub. Given the hassle I had finding info for radium chloride, which certainly is a well defied compound, I can't see us having anything to say on francium compounds that can't go in the main article. Physchim62 (talk) 09:01, 26 November 2008 (UTC)

It could just redirect to a Compounds of francium/Francium compounds article. 76.66.195.63 (talk) 12:40, 28 November 2008 (UTC)

Much simpler to make them redirect to Francium, given the sparcity of information. Physchim62 (talk) 13:01, 28 November 2008 (UTC)

Francium fluoride

Francium fluoride was WP:PRODded for deletion. 76.66.195.63 (talk) 12:38, 28 November 2008 (UTC)

Tagging high resolution PNG images with {{Convert to SVG|chemical}} on Commons

Any opinions concerning my suggestion made on Commons:Category talk:Chemical images that should use vector graphics (please discuss there)? --Leyo 19:52, 1 December 2008 (UTC)

BTW: I just noticed that there are also a few hi reg images in the “local” Category:Chemical images that should be in SVG format. It might be best to move them to Commons instead to simply untag them. --Leyo 21:15, 1 December 2008 (UTC)

I just proposed the deletion of that category... Input would be welcome. Cacycle (talk) 23:01, 5 December 2008 (UTC)

I have started to remove high resolution PNG images from the category, but it will take some time until that work will be finished. Help is welcomed. --Leyo 03:48, 20 December 2008 (UTC)

Do we have a guideline as to what is sufficiently high resolution, and what is not? --JaGa^talk 21:33, 20 December 2008 (UTC)

See WP:CSDG#General, but IMHO it's also dependent on the size of a structure. --Leyo 00:32, 21 December 2008 (UTC)

Silver hydroxide

Since this compound is not very stable, and since it exists primarily in an equilibrium with silver oxide, how about a merge there? --Rifleman 82 (talk) 13:21, 2 December 2008 (UTC)

Yes, I think a merge would be a good idea. As I understand it, it's a compound that (I believe) doesn't exist in pure form, and unlike things like calcium bicarbonate it's not highly important, so I don't think warrants having its own separate page. Walkerma (talk) 04:51, 5 December 2008 (UTC)

I agree with the proposed merge. I started this article for reasons that I forget but are not compelling. We have articles on related species that are invoked but are even less "real" - silicic acid and titanic acid, which probably should be incorporated into silica and titanium dioxide.--Smokefoot (talk) 05:00, 5 December 2008 (UTC)

Potassium carbonate

Sanity check for the spacefill model? I'm expecting some sort of crystal lattice comprising K⁺ and CO₃^2-, not an covalent K-O bond. --Rifleman 82 (talk) 16:16, 6 December 2008 (UTC)

Depicting ionic compounds graphically can be a bit tricky. It could be argued that the 2D skeletal structure is deficient because it doesn't convey information about the true solid structure. But at least it conveys important connectivity information. When it comes to a 3D structure, however, I don't think ionic compounds should be depicted like the one currently in potassium carbonate, because a 3D structure should convey more than just connectivity information. An image depicting a crystal lattice would be ideal, but the current image adds no useful information to the article and could certainly be considered inaccurate. I would prefer to see it removed. -- Ed (Edgar181) 20:02, 6 December 2008 (UTC)

I agree that this should not be done this way. However, it would be nice to show the 3-D structures of polyatomic ions, e.g. to illustrate the symmetric trigonal planar structure of the carbonate anion. Cacycle (talk) 00:05, 7 December 2008 (UTC)

I've been working on an image of the crystal structure of K₂CO₃ for Potassium carbonate, should be ready soon. There is a 3D pic of the carbonate ion at Carbonate.

I think 2D structures can be useful for ionic compounds, as seen in Ammonium nitrate and Ammonium carbonate - they take much less time to understand than an image of the crystal lattice and the stoichiometry is often clearer.

Ben (talk) 13:29, 7 December 2008 (UTC)

OK, new image is in place at Potassium carbonate.

Ben (talk) 01:01, 9 December 2008 (UTC)

Very nice! Thank you. -- Ed (Edgar181) 02:09, 9 December 2008 (UTC)

Dioxin

Given the scariness of Irish pigs these days, this may be of interest to anyone that can offer advice or clean up the page a bit. Cheers, Freestyle-69 (talk) 02:54, 9 December 2008 (UTC)

Image:NisinStructure.gif

Someone wrote to OTRS to let us know that this image is incorrect, they said: "This graphic is wrong. Wrong amino acid in N-terminal position.". Can someone take a look at it & fix if necessary? Thanks, --Versageek 05:20, 9 December 2008 (UTC)

There is something wrong: the figure has a valine at that position but the sequence at the bottom says isoleucine. I don't know which is right, and there are other apparent mismatches where the non-standard aminoacids are labeled with standard names. --Itub (talk) 08:14, 9 December 2008 (UTC)

There are a couple of errors in that structure. I created a new image which I believe is correct based on PubChem, Chemical Abstracts, and one of the papers cited in the article. I also added to nisin a Chembox and a 3D image from the German Wikipedia article. -- Ed (Edgar181) 13:12, 9 December 2008 (UTC)

Molybdopterin

Can someone with access to doi:10.1016/S0162-0134(98)10054-5 please check the molybdopterin article? I'm a bit uncomfortable with the current state of the article, and especially with my structures. I am unsure whether molybdopterin is currently used to refer to the molybdenum-bound pyranopterin ring (as my images show) or to the "open" pyranopterin system (as most databases show), with the molybdenum-bound form simply called a molybdenum cofactor.

I had a nice chat with PatríciaR (talk · contribs) about it this September (at Commons, in Portuguese unfortunately) and she noted that a) the nomenclature is still poorly defined and b) current consensus seems to agree with the structures in the article (that is, molybdopterin is acceptable as a name for the molybenum-bound cofactor). If someone could take the time to review the article I linked above and make modifications on our end as necessary, I would really appreciate it; my PC is still acting up, and I haven't even been able to keep up our curation efforts lately. Best, Fvasconcellos (t·c) 15:35, 13 December 2008 (UTC)

My fairly certain understanding is that the cofactor does not contain Mo, so the caption would ideally be revised. Molybdopterins bind tungsten too. I will edit the report later.--Smokefoot (talk) 15:57, 13 December 2008 (UTC)

End of semester projects?: now its Intro to Astrochemistry

Some monster edits at ammonia, formaldehyde, and hydrogen cyanide. Although many of us like this theme, the contributions seem overly specialized - do others agree? I tried contacting two of the students, but they are unresponsive. Suggestions?--Smokefoot (talk) 23:31, 16 December 2008 (UTC)

I only briefly looked at the additions to ammonia, but I agree most, maybe even all of the new info is way too specialized. I think it should be cut out and put into a sub-page called interstellar chemistry of ammonia or something like that. Yilloslime (t) 00:05, 17 December 2008 (UTC)

Agree. I saw the edits to formaldehyde. It was referenced and obviously a whole load of work, but it sorta swamps the main article. Freestyle-69 (talk) 07:41, 18 December 2008 (UTC)

I think it's great that we have someone to add all this information, but I also agree that it would be best to spin it off in WP:Summary style to have a more balanced main article. --Itub (talk) 00:22, 19 December 2008 (UTC)

Molecular formula vs. structural formula

This edit to acetone points out a possible flaw in the new method of representing substances. The method simplifies editing, and auto-calculates MW, but there seems to be no way of still representing the molecule as CH₃COCH₃. The way I see it, a text-type structural formula is more informative than a simple molecular formula. Granted, we do have one or more diagrams at the top of the chembox, so I don't think it's a big deal, but worth raising. Anyone have any thoughts on this? Cheers, Freestyle-69 (talk) 21:48, 21 December 2008 (UTC)

I agree that structural formulae are preferrable. But for the ChemBox we have just used empirical formulae, following the Hill system (C, then H, then alphabetical). In the lead-off paragraph, usually the first sentence, I have been presenting structural formulas, such as (CH₃)₂CO or CH₃C(O)CH₃. In this way, readers see two kinds of formula and can take the one that is most useful for them.--Smokefoot (talk) 23:39, 21 December 2008 (UTC)

Yup, I've seen the strucforms in the leads of some articles, and I like it- I'll make a point to add them if it's relevant. Thanks, Freestyle-69 (talk) 22:25, 23 December 2008 (UTC) And everyone have a safe and happy xmas/festive season/vacation/holiday/other-politically-correct-alternative :)

"Nitrogen tritoxide"

I noticed this on the page listing requested articles. Is there really such a thing? A google search suggests it's a typo of nitrogen tetroxide. --Rifleman 82 (talk) 10:06, 23 December 2008 (UTC)

My guess is that "Nitrogen tritoxide" is a typographical error. I consulted the bible (Holleman and Wiberg) and indeed a substantial body of work appears to exists for nitrogen trioxide, one form of which is the adduct of NO and O2, en route to NO2.--Smokefoot (talk) 18:32, 23 December 2008 (UTC)

The request was for titroxide, not tritoxide, so the title of this section is a second-degree typo. ;-) I think titroxide is most likely a typo for tetroxide, like google suggests. --Itub (talk) 18:41, 23 December 2008 (UTC)

4-Aminopyridine: why change the article name?

I am curious about the justification for retitling 4-aminopyridine to "Fampridine". My intial philosophical concern is that drugs are chemical compounds, but by replacing chemical names with drug names, we are dumbing down the chemistry. People taking these drugs are, to some extent, deluded into thinking that they are not ingesting real chemicals but some sort of candy. In other words, the practice could be seen as anti-scientific. But maybe I am off-base and too cynical. On the other hand, aspirin trumped acetylsalicylic acid (I would recommend that the redirects go from aspirin to acetylsalicylic acid). It seems that we should adopt some policy on this topic. I recently renamed the obsolete drug "Atoxyl" to arsanilic acid.--Smokefoot (talk) 18:32, 23 December 2008 (UTC)

For drugs, we generally use the INN. In most cases I think this is a good idea because the systematic chemical names are usually unwieldy. 4-aminopyridine may be one of the few where the chemical name is relatively easy to remember, spell, and pronounce. In this case the question may be whether this should be treated primarily as a "chemical" or as a "drug", because the different wikiprojects have different naming conventions. --Itub (talk) 18:49, 23 December 2008 (UTC)

This one seems to be the latest spam attack we have had from the drug companies. As the article itself states, 4-aminopyridine is currently in phase III clinical trials: in other words, it is not yet released onto the market and so there is no reason for calling it by a name which only specialists would know (even if the INN is accurate, I didn't even bother to check). Such moves to give such blatant advanced wikipublisity to prospective pharamceuticals should, IMHO, be beaten back by anyone who spots it. Physchim62 (talk) 19:22, 23 December 2008 (UTC)

Relax, the article was renamed by fvasconcellos (talk · contribs), one of the major contributors of the drugs wikiprojects and according to their style guide. I suggest you take your concerns to him instead of constructing conspiracy theories. --Itub (talk) 20:28, 23 December 2008 (UTC)

Please relax. An International Nonproprietary Name is the very opposite of publicity—as the name "nonproprietary" implies. Its purpose is to reduce confusion, and to prevent drugs being referred to solely by their trade names. As for "prospective pharmaceutical", I have learned that 4-AP has long been used in the symptomatic management of multiple sclerosis, and it has had orphan drug status in the U.S. for years (IIRC) for this very indication. (In the EU, it has orphan status for the treatment of Guillain-Barré syndrome.) Just because a drug company is taking an interest and pushing for marketing approval does not mean my edit was an attempt at "wikipublicity" (I'll have to remember that one :)

Smokefoot, we already have policy (rather, guideline) on this topic. Renaming drug articles to their subject's INN is part of the Manual of Style on medicine-related articles, and therefore overrides our convention of naming articles after the most common designation of their subject as per Wikipedia:Naming conventions (common names)#Exceptions. It's a good guideline and a very useful one—surely you wouldn't have paracetamol renamed N-(4-hydroxyphenyl)acetamide! Furthermore, INNs are always unambiguous, as that is that very purpose. Trade names can be ambiguous (not to mention ludicrous at times) and I cannot imagine using them on Wikipedia—now that would be spam. Even in IUPAC names, while unambiguous, provide a certain leeway as they are based on recommendation and not policy; is dapsone 4-[(4-aminobenzene)sulfonyl]aniline or 4,4′-sulfonyldianiline?

In short, this should have been a textbook example of an uncontroversial move—supported (if not mandated) by guideline and regarding a completely uncontroversial article. I apologize if anyone was offended (or driven to philosophical considerations :), but there is absolutely no reason to be. Seriously. Fvasconcellos (t·c) 20:48, 23 December 2008 (UTC)

By the way, my very multi-religious family is about to kindle the lights for Hanukkah, and I am off to join them as I do every year. If anyone would like further clarification, I'll be back later today. Fvasconcellos (t·c) 20:55, 23 December 2008 (UTC)

I'm not creating conspiracy theories: I have seen one multinational pharmaceutical company edit an article (sloppily, from a traceable IP address) then release the drug onto the market the very same week citing the WP article in the press release! It certainly made for an interesting luchtime's editing and emailing.

As for 4-aminopyridine, it is not (yet) a drug: it is in phase III trials. As it has an INN and was granted "orphan" status, it has presumably been used in the past, but for what we don't know. At the moment, we can hardly say that it is primarily a drug; the only evidence we have is that someone thinks it might help patients with Guillain-Barré syndrome. Nothing else in the article allows us to say that it is anything other than a simple organic compound, and so there seems no reason to move the page just because it has an INN. as WP:NCCHEM notes, "no set of guidelines can cover every case". Physchim62 (talk) 22:07, 23 December 2008 (UTC)

WP:NCCHEM also notes "Where a compound has a WHO International Nonproprietary Name (INN), this should be used as the article title." Never mind; I have no personal preference either way. I would request a move, but it appears we already have a rough consensus against it. I have been meaning to move Hydroxyurea to Hydroxycarbamide for quite some time, as it is in de-WP; would you take issue with that? (Seriously, I'd like to know your opinion.) Fvasconcellos (t·c) 13:33, 24 December 2008 (UTC)

• we are supposed to request a move , then discuss a move and then execute a move after a consensus is reached. Too often editors just move regardless V8rik (talk) 22:26, 23 December 2008 (UTC)
  • Actually, that is not necessary; what happened to WP:BOLD? :) Moves need only be discussed when their value is disputable (as it has clearly become in this case). Fvasconcellos (t·c) 13:33, 24 December 2008 (UTC)
    • I checked WP:BOLD and it does not apply to moves. Moves are supposed to work like mergers. Start with placing a relevant tag and open discussion. V8rik (talk) 17:33, 24 December 2008 (UTC)

In cases where a compound is primarily known for its chemical use and under its chemical name it is counterproductive to move the article to its less-notable drug name per Wikipedia:Naming_conventions#General_conventions. We might want to clarify that at Wikipedia:Manual of Style (medicine-related articles). Cacycle (talk) 00:29, 24 December 2008 (UTC)

Well, WP:COMMONNAME only applies "Except where other accepted Wikipedia naming conventions give a different indication". How do you think we could go about determining the primary use of a compound—medical vs. chemical? Fvasconcellos (t·c) 13:33, 24 December 2008 (UTC)