Wikipedia talk:WikiProject Chemicals

Chembox: adding AITS spectral database external link (SDBS)

• See Wikipedia talk:WikiProject Chemistry § Linking Chembox to spectroscopic data on the AITS database (AITS: SDBS database external link).

DePiep (talk) 11:46, 19 January 2023 (UTC)

Articles with long titles

When the title of an article is too long and it doesn't contain any hyphens enabling a line break, there might be a layout issue: The chembox is then moved to the left (see e.g. Methoxymethylenetriphenylphosphorane). These articles might be affected: hastemplate:chembox intitle:/[A-Z\(\)]{33}/i (redirects filtered out) --Leyo 08:09, 20 January 2023 (UTC)

I cannot reproduce this on my browser, Google Chrome in macOS Monterey. –LaundryPizza03 (dc̄) 08:23, 20 January 2023 (UTC)

At the even longer title Phosphoribosylaminoimidazolesuccinocarboxamide (46 letters), it just made the chembox wider than, say, Pyran (5 letters). –LaundryPizza03 (dc̄) 08:28, 20 January 2023 (UTC)

I use Firefox. In Edge, it is the same as you describe for Google Chrome. Anyway, both widening the chembox and moving it leftwards is undesirable. --Leyo 10:52, 20 January 2023 (UTC)

(ec) How should the chembox handle this? Hard to automate, better require an editor to add {{SHY}}. We could start with categorising when title length > n. DePiep (talk) 11:24, 20 January 2023 (UTC)

Applied {{SHY}} to |Name=. See Methoxymethylenetriphenylphosphorane [1] (at the right place?) DePiep (talk) 11:26, 20 January 2023 (UTC)

@Leyo @LaundryPizza03 @DePiep The problem is easily solved by using the |Name parameter to give the image a shorter name and override the default. I've just done that for Phosphoribosylaminoimidazolesuccinocarboxamide, so you can see the result. Mike Turnbull (talk) 11:26, 20 January 2023 (UTC)

See also 5′-Phosphoribosyl-4-carboxy-5-aminoimidazole: these automated breaks are OK right away? -DePiep (talk) 11:30, 20 January 2023 (UTC)

And DePiep's alternative using {{SHY}} is also fine if you instead want to add a hyphen. Mike Turnbull (talk) 11:30, 20 January 2023 (UTC)

@DePiep and Michael D. Turnbull: Thanks. Have you gone through the whole list? Or have you got a search link with less false positives? --Leyo 22:51, 22 January 2023 (UTC)

re Leyo. I changed the regex (add \d etc), found ca. 850 article titles of which 600 are redirects. Resulting List is at User:DePiep/sandbox2. Also in therekept some ~50 really long Redirect names (because: in target article, is the infobox title shortened for this wrong reason?). Redlinks must be typo's from my cleanup. (Source cannot output raw datalist).

It's yours to use (c/p), I don't have time to check them. DePiep (talk) 07:24, 23 January 2023 (UTC)

Thank you. There seem to be quite some with hyphens (i.e. an optional line break). --Leyo 10:41, 23 January 2023 (UTC)

@Leyo, @DePiep I've extracted DePiep's list into an Excel spreadsheet and easily found the names where there is already a hyphen or a blank that allows the names to line-break automatically and hence no need for the {{shy}} trick. I'll go through all 86 articles that I have found which do need a soft hyphen and put one in. I should easily complete this today. Mike Turnbull (talk) 11:38, 23 January 2023 (UTC)

Yes, formal in-name true character U+002D - HYPHEN-MINUS will do some linebreaking already. But it is my impression that these (chemistry name induced) hyphens might be positioned bad for linebreaking. Again, {{SHY}} is our friend. DePiep (talk) 11:39, 23 January 2023 (UTC)

OK all done, I think. Any left over can be done as people spot them. Mike Turnbull (talk) 12:32, 23 January 2023 (UTC)

Thank you. I found 18 additional articles that I changed accordingly. --Leyo 16:43, 23 January 2023 (UTC)

Long ago when chembox validation was getting started, we centralized on not inserting anything that would make the display appear different than the actual name, in order to improve discoverability from external search-engines. DMacks (talk) 10:49, 23 January 2023 (UTC)

1. By adding {{SHY}} in |Name=, the article title is not changed.

2. The external search argument is handled by {{DISPLAYTITLE}}. {{Chembox}} is not to make exceptions in this. DePiep (talk) 11:31, 23 January 2023 (UTC)

Should certain organic compounds have a "Variants" section?

Inorganic compounds like sodium chloride often have a short "Related compounds" section in their infobox, because there are only so many related binary salts you can make. Lithium chloride, potassium chloride, sodium fluoride, sodium bromide, etc. This isn't practical for organic compounds though, because there's hundreds to thousands of different variations of an organic compound, just from different functional groups you can add on, isomers. Should "base" organic compounds have a variants section, containing variants which have articles, which can be moved into a separate article if it gets long enough? For examples I just made, see Phenylacetic acid, Dibenzyl ketone, and Tetraphenylcyclopentadienone. This would help make articles easier to find by weaving the web of links. Then hypothetically long lists could be moved to e.g. "List of phenylacetic acid variants". Michael7604 (talk) 21:03, 20 January 2023 (UTC)

@Michael7604 I don't like that idea: as well as the reason you mention, "variants" are in the eye of the beholder. To take a specific example, acetone does have a "related compounds" section which currently has Butanone, Isopropyl alcohol, Formaldehyde, Urea and Carbonic acid. To my eye, the relationship between acetone and urea is tenuous at best and downright misleading at worst. Professional organic chemists use the word analog in a way that is still not very precise but usually refers to some sort of Markush structure, especially in relation to patents. Mike Turnbull (talk) 22:32, 20 January 2023 (UTC)

One idea, maybe the criteria being counted as a "related compound" could be if the name contains the main compound. E.g., 4-bromophenyl acetic acid contains "phenylacetic acid". One of the names of butanone, "methylacetone", contains "Acetone". But isopropyl alcohol has nothing to do with "acetone". This would also apply if the name gets split up, e.g. Bis(4-bromobenzyl) ketone is a variant of Dibenzyl ketone. With this criteria just adding a functional group to a molecule always makes it a related compound. One way or another there should be a way for curious readers to learn about similar compounds, since mobile readers can't see categories. Michael7604 (talk) 22:40, 20 January 2023 (UTC)

That would be a good argument for getting the mediawiki folk to add such a facility. Note that we do have a system of templates that is much superior, in my opinion. Hence for a herbicide like 2,4-D, the only "related compound" in the chembox is 2,4,5-T but at the bottom of the article there's a template {{herbicides}} that does a very good job of linking to relevant additional articles. Mike Turnbull (talk) 22:56, 20 January 2023 (UTC)

@Michael D. Turnbull Footer templates aren't visible for mobile either, that is why it is important to weave the web with links in article bodies. Michael7604 (talk) 23:05, 20 January 2023 (UTC)

First, proposals like this are healthy, so thank you Michael7604. Second, however, I'm 95% with Michael D. Turnbull on being opposed. One reason is that selection of variants is just too subjective. And the idea invites contributions from editors who know isolated factoids but lack an appreciation of the landscape of organic chemistry. Then the handful of knowledgeable editors would be forced into doing a lot more pruning vs content creation, our prime mission. On the other hand, there is nothing to stop an editor from adding an ad hoc "related compound" as someone did today on 2-octanone by noting its relevance to filbertone. Filbertone is not really a variant, but the link nicely complements our article, IMHO.--Smokefoot (talk) 23:56, 20 January 2023 (UTC)

This "variant" problem is worse in simple aromatic rings. Some articles like oxazole basically hard to separate the parent compound and everything that have this ring. --Nucleus hydro elemon (talk) 09:37, 21 January 2023 (UTC)

Unreviewed Featured articles year-end summary

Unreviewed featured articles/2020/4Q2022

Restoring older Featured articles to standard: year-end 2022 summary Unreviewed featured articles/2020 (URFA/2020) is a systematic approach to reviewing older Featured articles (FAs) to ensure they still meet the FA standards. A January 2022 Signpost article called "Forgotten Featured" explored the effort. Progress is recorded at the monthly stats page. Through 2022, with 4,526 very old (from the 2004–2009 period) and old (2010–2015) FAs initially needing review: 357 FAs were delisted at Featured article review (FAR). 222 FAs were kept at FAR or deemed "satisfactory" by three URFA reviewers, with hundreds more being marked as "satisfactory", but awaiting three reviews. FAs needing review were reduced from 77% of total FAs at the end of 2020 to 64% at the end of 2022. Of the FAs kept, deemed satisfactory by three reviewers, or delisted, about 60% had prior review between 2004 and 2007; another 20% dated to the period from 2008–2009; and another 20% to 2010–2015. Roughly two-thirds of the old FAs reviewed have retained FA status or been marked "satisfactory", while two-thirds of the very old FAs have been defeatured. Entering its third year, URFA is working to help maintain FA standards; FAs are being restored not only via FAR, but also via improvements initiated after articles are reviewed and talk pages are noticed. Since the Featured Article Save Award (FASA) was added to the FAR process a year ago, 38 FAs were restored to FA status by editors other than the original FAC nominator. Ten FAs restored to status have been listed at WP:MILLION, recognizing articles with annual readership over a million pageviews, and many have been rerun as Today's featured article, helping increase mainpage diversity. Examples of 2022 "FAR saves" of very old featured articles Solar System 2007 FA J. K. Rowling 2007 FA June 26, 2022 TFA Antarctica 2006 FA Joan of Arc 2006 FA Speed of light 2010 FA All received a Million Award But there remain almost 4,000 old and very old FAs to be reviewed. Some topic areas and WikiProjects have been more proactive than others in restoring or maintaining their old FAs. As seen in the chart below, the following have very high ratios of FAs kept to those delisted (ordered from highest ratio): Biology Physics and astronomy Warfare Video gaming and others have a good ratio of kept to delisted FAs: Literature and theatre Engineering and technology Religion, mysticism and mythology Media Geology and geophysics ... so kudos to those editors who pitched in to help maintain older FAs ! FAs reviewed at URFA/2020 through 2022 by content area FAs reviewed at URFA/2020 from November 21, 2020 to December 31, 2022 (VO, O) Topic area Delisted Kept Total Reviewed Ratio Kept to Delisted (overall 0.62) Remaining to review for 2004–7 promotions Art, architecture and archaeology 10 6 16 0.60 19 Biology 13 41 54 3.15 67 Business, economics and finance 6 1 7 0.17 2 Chemistry and mineralogy 2 1 3 0.50 7 Computing 4 1 5 0.25 0 Culture and society 9 1 10 0.11 8 Education 22 1 23 0.05 3 Engineering and technology 3 3 6 1.00 5 Food and drink 2 0 2 0.00 3 Geography and places 40 6 46 0.15 22 Geology and geophysics 3 2 5 0.67 1 Health and medicine 8 3 11 0.38 5 Heraldry, honors, and vexillology 11 1 12 0.09 6 History 27 14 41 0.52 38 Language and linguistics 3 0 3 0.00 3 Law 11 1 12 0.09 3 Literature and theatre 13 14 27 1.08 24 Mathematics 1 2 3 2.00 3 Media 14 10 24 0.71 40 Meteorology 15 6 21 0.40 31 Music 27 8 35 0.30 55 Philosophy and psychology 0 1 1 – 2 Physics and astronomy 3 7 10 2.33 24 Politics and government 19 4 23 0.21 9 Religion, mysticism and mythology 14 14 28 1.00 8 Royalty and nobility 10 6 16 0.60 44 Sport and recreation 32 12 44 0.38 39 Transport 8 2 10 0.25 11 Video gaming 3 5 8 1.67 23 Warfare 26 49 75 1.88 31 Total 359 Note A 222 Note B 581 0.62 536 Noting some minor differences in tallies: A URFA/2020 archives show 357, which does not include those delisted which were featured after 2015; FAR archives show 358, so tally is off by at least one, not worth looking for. B FAR archives show 63 kept at FAR since URFA started at end of Nov 2020. URFA/2020 shows 61 Kept at FAR, meaning two kept were outside of scope of URFA/2020. Total URFA/2020 Keeps (Kept at FAR plus those with three Satisfactory marks) is 150 + 72 = 222. But looking only at the oldest FAs (from the 2004–2007 period), there are 12 content areas with more than 20 FAs still needing review: Biology, Music, Royalty and nobility, Media, Sport and recreation, History, Warfare, Meteorology, Physics and astronomy, Literature and theatre, Video gaming, and Geography and places. In the coming weeks, URFA/2020 editors will be posting lists to individual WikiProjects with the goal of getting these oldest-of-the-old FAs reviewed during 2023. Ideas for how you can help are listed below and at the Signpost article. Review a 2004 to 2007 FA. With three "Satisfactory" marks, article can be moved to the FAR not needed section. Review "your" articles: Did you nominate a featured article between 2004 and 2015 that you have continuously maintained? Check these articles, update as needed, and mark them as 'Satisfactory' at URFA/2020. A continuously maintained FA is a good predictor that standards are still met, and with two more "Satisfactory" marks, "your" articles can be listed as "FAR not needed". If they no longer meet the FA standards, please begin the FAR process by posting your concerns on the article's talk page. Review articles that already have one "Satisfactory" mark: more FAs can be indicated as "FAR not needed" if other reviewers will have a look at those already indicated as maintained by the original nominator. If you find issues, you can enter them at the talk page. Fix an existing featured article: Choose an article at URFA/2020 or FAR and bring it back to FA standards. Enlist the help of the original nominator, frequent FA reviewers, WikiProjects listed on the talk page, or editors that have written similar topics. When the article returns to FA standards, please mark it as 'Satisfactory' at URFA/2020 or note your progress in the article's FAR. Review and nominate an article to FAR that has been 'noticed' of a FAR needed but issues raised on talk have not been addressed. Sometimes nominating at FAR draws additional editors to help improve the article that would otherwise not look at it. More regular URFA and FAR reviewers will help assure that FAs continue to represent examples of Wikipedia's best work. If you have any questions or feedback, please visit Wikipedia talk:Unreviewed featured articles/2020/4Q2022.

FAs last reviewed from 2004 to 2007 of interest to this WikiProject

If you review an article on this list, please add commentary at the article talk page, with a section heading == [[URFA/2020]] review== and also add either Notes or Noticed to WP:URFA/2020A, per the instructions at WP:URFA/2020. Comments added here may be swept up in archives and lost, and more editors will see comments on article talk. SandyGeorgia (Talk) 21:11, 20 January 2023 (UTC)

1. Enzyme kinetics
2. Francium
3. Joseph Priestley
4. Nicotinamide adenine dinucleotide
5. Oxidative phosphorylation
6. Uranium
7. Xenon

Psilocybin Featured article review

User:DigitalIceAge has nominated Psilocybin for a featured article review here. Please join the discussion on whether this article meets the featured article criteria. Articles are typically reviewed for two weeks. If substantial concerns are not addressed during the review period, the article will be moved to the Featured Article Removal Candidates list for a further period, where editors may declare "Keep" or "Delist" in regards to the article's featured status. The instructions for the review process are here. SandyGeorgia (Talk) 11:25, 24 January 2023 (UTC)

Good article reassessment for Iron(III) chloride

Iron(III) chloride has been nominated for a good article reassessment. If you are interested in the discussion, please participate by adding your comments to the reassessment page. If concerns are not addressed during the review period, the good article status may be removed from the article. Nucleus hydro elemon (talk) 08:16, 27 January 2023 (UTC)

Discussion at WP:MCQ § Proactive request for input

 You are invited to join the discussion at WP:MCQ § Proactive request for input. -- Marchjuly (talk) 19:42, 23 February 2023 (UTC)

Project-independent quality assessments

Quality assessments are used by Wikipedia editors to rate the quality of articles in terms of completeness, organization, prose quality, sourcing, etc. Most wikiprojects follow the general guidelines at Wikipedia:Content assessment, but some have specialized assessment guidelines. A recent Village pump proposal was approved and has been implemented to add a |class= parameter to {{WikiProject banner shell}}, which can display a general quality assessment for an article, and to let project banner templates "inherit" this assessment.

No action is required if your wikiproject follows the standard assessment approach. Over time, quality assessments will be migrated up to {{WikiProject banner shell}}, and your project banner will automatically "inherit" any changes to the general assessments for the purpose of assigning categories.

However, if your project has decided to "opt out" and follow a non-standard quality assessment approach, all you have to do is modify your wikiproject banner template to pass {{WPBannerMeta}} a new |QUALITY_CRITERIA=custom parameter. If this is done, changes to the general quality assessment will be ignored, and your project-level assessment will be displayed and used to create categories, as at present. Aymatth2 (talk) 13:19, 10 April 2023 (UTC)

Stylized depiction of chemical structures

IMHO the dot structures found e.g. in Croconate blue, Croconate violet, Oxocarbon, Peroxydicarbonate, 1,3-Bis(dicyanomethylene)squarate and 1,2-Bis(dicyanomethylene)squarate do not comply with MOS:CHEM. Leyo 15:09, 18 April 2023 (UTC)

Agreed. They seem to have been added by Jorge Stolfi. The one I checked was done in 2010. Jorge seems to still be active (last edit this March) so perhaps he would like to change the drawings to more conventional ones, or I can do that if he is no longer interested. Mike Turnbull (talk) 16:23, 18 April 2023 (UTC)

I have now redrawn the individual compounds Croconate blue, Croconate violet, 1,3-Bis(dicyanomethylene)squarate and 1,2-Bis(dicyanomethylene)squarate. Another I've changed is 2-(Dicyanomethylene)croconate. The oxocarbon article has lots of drawing that are consistent, although not aligned with usual conventions, and I've left that alone, along with peroxydicarbonate. Mike Turnbull (talk) 15:59, 21 April 2023 (UTC)

Though perhaps the different image version should have a different name. Graeme Bartlett (talk) 12:10, 22 April 2023 (UTC)

@Graeme Bartlett I would have done that if any of the articles in which the diagrams were used had a reason to retain the old images but I could see no justification for that in MOS:CHEM. Of course, if the earlier versions were needed, they can easily be obtained from the Commons history and I would have no objections if my overwrites were reverted in that case. Mike Turnbull (talk) 17:19, 22 April 2023 (UTC)

That's not allowed by commons guidelines (commons:COM:OVERWRITE). Images that are substantively different need to be uploaded at a different filename. Please undo/revert those changes there. DMacks (talk) 18:15, 22 April 2023 (UTC)

c:COM:SPLIT exists to handle those cases while preserving history and avoiding unnecessary complications. –LaundryPizza03 (dc̄) 18:39, 22 April 2023 (UTC)

Thanks for the link. I've put in the splitting requests. Mike Turnbull (talk) 20:49, 22 April 2023 (UTC)

For the record, in order of amount of total work required: someone else handling your split-request > you re-uploading at a different name and reverting the old filename's contents > you filing a split-request. DMacks (talk) 03:42, 23 April 2023 (UTC)

I don't feel strongly about my diagrams in general. If someone wishes to redo them, please go ahead. But may I suggest better ways to spend that time. For example, last I checked there were dozens of fatty acid diagrams, used in dozens of articles, with the omega labels just wrong.
However, the new croconate diagrams, in particular, seem less informative than mine, and somewhat misleading. First, the convention that "unlabeled corners and ends are carbon atoms", while fully internalized by chemists, is quite confusing to a large section of the target public. Moreover, the new diagrams hide the aromatic character of the ring, and the "fractional" bonds and negative charges on the attached carbons that makes it work. (At least, that was the structure I gleaned from the papers I read.) The new image is just one of the "resonance" forms, isn't that so? And "resonance" is just a hack to fit the actual messy orbital truth into the old model of integer valences, localized integer charges, and binary bonds; isn't that so? For these reasons, shouldn't my diagrams (or others equivalent to them, e.g. 3D ball-and-stick) be kept as alternate representations, at least?
Finally, please note that uniformity of style and looks -- which is basically what the MOS is about -- has very little value for the reader. A commercial paper encyclopedia (dictionary, textbook, etc) must have strictly uniform style and typesetting, because otherwise the prospective buyer, leafing through it, would think that it is a mash-up of texts by disparate authors, randomly edited, with no plan and no oversight by a chief editor. But Wikipedia is a mash-up of texts by disparate authors, randomly edited, with no plan and no oversight by a chief editor. Thus, uniformizing its style and typesetting is downright dishonest: it leads the reader to think that Wikipedia is more reliable and complete than it actually is...
Methinks that the only "manual of style" that an editor needs to know is "look at a few other articles on related subjects, try to imitate what is good in them, and try to fix was is bad."
All the best, Jorge Stolfi (talk) 21:37, 24 April 2023 (UTC)

We chemists usually show the most representative resonance structure when possible (we can all agree that we aren't going to emphasize minority resonance structures). True, one needs significant knowledge to understand nuances of resonance structures. With the major resonance structure at least a reader can count electrons, check for conformance of trends in oxidation states and electron counting rules (octet rule, etc), and anticipate sites on a chemical that will be basic/nucleophilic vs acidic/electrophilic vs saturated/unsaturated. One cannot readily undertake those analyses with stylized images.

In terms of "fully internalized by chemists, is quite confusing to a large section of the target public." Yes indeed. One needs a significant knowledge to read encyclopedia articles on specialized topics in chemistry. That is the way it is: Wikipedia presents facts. At the same time, we rely on discussions like this to review and perhaps recalibrate our communication styles. --Smokefoot (talk) 21:57, 24 April 2023 (UTC)

Of course it is OK to use specialized jargon (textual or graphical) in those parts of articles that will be only of interest to specialists. However, the target readership of Wikipedia (or any general encyclopedia) definitely includes every non-specialist who read the term "geomagnetic jerk" or "neutrino oscillation" and wants to know what that is. Thus every article should strive to satisfy those readers, to the level of detail that will be useful to them, as well as the specialists. All the best, Jorge Stolfi (talk) 15:21, 25 April 2023 (UTC)

@Jorge Stolfi You make some interesting points. My view is that no encyclopaedia, even Wikipedia, can comment on the complexity of aromaticity and resonance forms in every article in which it is relevant. We do so occasionally, as at the archetype, benzene, where the diagram I've placed here is included and does cover these issues.

Benzene Representations

For better or worse, our MOS:CSDG specifies using a molecule editor and ACS drawing conventions. All these standard editors give Kekule-style representations of aromaticity and chemical drawings in Wikipedia mainly conform to these widespread standards also seen in Chemspider and Pubchem and virtually every professional chemical publication. My main concern with your drawings of the croconate examples, aside from the MOS, was that they didn't sufficiently emphasise that these are dianions: no charges are shown (see example below) and that outweighed the fact that they show the aromaticity better, albeit somewhat unconventionally.

Croconate violet, ACS conventions

Croconate violet, Stolfi

However, I was certainly in error when I overwrote your files and that has now been undone. There may well be a case for expanding the Pseudo-oxocarbon anion article to use both types of diagram. Currently it has only mine. Mike Turnbull (talk) 11:46, 25 April 2023 (UTC)

Problem images

Jorge Stolfi I'm not sure if you are aware, but there are ways of flagging images that have issues on Commons (like these fatty acid diagrams). Sadly these don't yet feed into our Alerts list --Project Osprey (talk) 09:00, 25 April 2023 (UTC)

Thanks! Jorge Stolfi (talk) 15:10, 25 April 2023 (UTC)

• Commons:WikiProject Chemistry/Deletion requests
• Commons:Category:Disputed chemical diagrams, /expired
• Commons:Category:Low quality chemical diagrams, /expired
• Commons:Category:Verified chemical structure diagrams
• Commons:Category:Media needing chemical classification

Re: TOXNET has moved

(Continuation of Wikipedia talk:WikiProject Chemicals/Archive 2023#Re:_TOXNET_has_moved)

I just finished working on this. I moved {{HPD}} to {{CPID}} and updated the links on all pages that used it. Enjoy! — Garrett W. {☎ ✍} 18:54, 4 May 2023 (UTC)

Also just finished going through insource:/householdproducts\.nlm\.nih\.gov/ and updating all the broken links in those. — Garrett W. {☎ ✍} 20:30, 4 May 2023 (UTC)

Thank you. What about deleting the redirect Template:HPD? --Leyo 22:23, 14 May 2023 (UTC)

Sure, I could propose it for deletion.

(edit) Done. — Garrett W. {☎ ✍} 06:14, 15 May 2023 (UTC)