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Is secondary amino acid (d:Q107186791) is notable?

Should we create the article secondary amino acid? Otherwise we may redirect it to amino acid or imino acid. Amino acid is a hypernym of secondary amino acid. Obsolescent meaning of imino acid includes secondary amino acid. If it is not notable, what is the best redirection target? 2001:2D8:30A:682D:0:0:190E:F0A4 (talk) 15:43, 11 June 2021 (UTC)

We might have to edit Template:Proteinogenic amino acids too. 2001:2D8:30A:682D:0:0:190E:F0A4 (talk) 15:47, 11 June 2021 (UTC)

Apart from this problem, I think that tertiary amino acid is not notable but we should redirect it to Non-proteinogenic amino acids. 2001:2D8:30A:682D:0:0:190E:F0A4 (talk) 15:52, 11 June 2021 (UTC)

Proline is the only (natural) amino acid that is a secondary amino acid. So the redirect could go there, or just to amino acid. I definitely would not support it redirecting to imino acid, as that is a short article about imines (-N= plus COOH). That article does, however, point out that Amino acids containing a secondary amine group (the only proteinogenic amino acid of this type is proline) are sometimes named imino acids, though this usage is obsolescent. Mike Turnbull (talk) 15:59, 11 June 2021 (UTC)

I'm not seeing any tertiary amino acids listed in non-proteinogenic amino acids, nor many secondary ones for that matter. If the term doesn't properly fit any article then a redirect probably isn't the right way to go. Is there any case for having such articles? They seem niche. --Project Osprey (talk) 16:53, 11 June 2021 (UTC)

If there are several secondary amino acids, we could have a list of secondary amino acids article. There is also hydroxyproline. Many drugs or alkaloids or their oxidised derivatives could be secondary or tertiary amino acids, but not notable or defined as such. Which also means that a category is not useful. Graeme Bartlett (talk) 22:23, 11 June 2021 (UTC)

English Wikipedia has at least four article about secondary amino acids: proline, hydroxyproline, pipecolic acid and sarcosine. Secondary amino acids have different behaviors than primary amine acids in analytic chemistry. There are about 4200 academic articles about secondary amino acids. This estimate is fouded by searching "secondary amino acid" OR "secondary amino acids" in Google Scholar. Same search of proteinogenic amino acid gives 17500 results in Google Scholar. However I have no confidence about the notability of secondary amino acid. 2001:2D8:E126:2E57:0:0:3200:10A0 (talk) 10:04, 12 June 2021 (UTC)

I found subclasses of secondary amino acids. N-methyl amino acids are secondary amino acids except few exceptions (e.g. n-methyl proline). English wikipedia has an article about n-methyl amino acids: N-methyl-L-amino-acid oxidase. If we create secondary amino acid§, we may redirect N-methyl amino acid to secondary amino acid. --2001:2D8:E359:2148:0:0:25C:4B45 (talk) 11:02, 12 June 2021 (UTC)

I found three more secondary amino acids (N-Methyl-D-aspartic acid, N-Methyl-L-glutamic acid, Azetidine-2-carboxylic acid) and one tertiary amino acids.(Dimethylglycine). English Wikipedia has at least 7 articles of secondary amino acid compounds --2001:2D8:E198:9507:0:0:1AE0:D0A0 (talk) 12:20, 12 June 2021 (UTC)

Please create secondary amino acid and Category:Secondary amino acids --2001:2D8:EB68:1DD5:0:0:155:CB45 (talk) 12:22, 15 June 2021 (UTC)

The 10 most-viewed, worst-quality articles according to this Wikiproject

• 32 Transparent wood composites 46,684 1,505 Stub Low
• 20 FOGBANK 55,211 1,781 Start Low
• 31 Rebis 47,562 1,534 Start Low
• 47 Liquid oxygen 39,800 1,283 Start High
• 57 Vantablack 36,998 1,193 Start Low
• 65 Nickel titanium 34,846 1,124 Start Mid
• 70 Smelling salts 34,047 1,098 Start Low
• 93 Alchemical symbol 30,256 976 Start Mid
• 96 Chemical formula 29,828 962 Start High
• 108 Titration 28,307 913 Start Top

Wikipedia:WikiProject Chemistry/Popular pages--Coin945 (talk) 06:58, 19 June 2021 (UTC)

Very helpful note. Fortunately (for the chemists), the above-cited articles are kinda peripheral from chemistry. Also these articles themselves are not travesties. Misleading information is what many of us are watching for. It would be great if we had that list. Also thin or missing topics.--Smokefoot (talk) 17:03, 19 June 2021 (UTC)

Most were underrated, and I have changed quite a few to C class. If I took the time to read, and assess, some of these could be rated B class. Graeme Bartlett (talk) 22:49, 19 June 2021 (UTC)

Draft:Organofluoride compounds

New in Draft world, Draft:Organofluoride compounds. Despite sounding like a rewrite of organofluorine chemistry this article actually covers the conversion of C-F into other groups, which I expect is notable in pharma. That notability is the only reason I'm flagging it here. Personally, I don't find it to be a good draft but someone might think it worth improving. Otherwise I'll move to reject. There are a 2-3 other drafts from around the same time which might indicated another class project. --Project Osprey (talk) 09:45, 22 June 2021 (UTC)

I'm not going to comment on the content but the images used are totally unacceptable since they are tiny .png which cannot be zoomed into enough to make them legible. Mike Turnbull (talk) 10:25, 22 June 2021 (UTC)

@Nwasfy: Its the usual graduate student cruft, admiring ultra-specialized details of reactions of interest to a fellow academicians occupying the same bubble. On one level, its nice that someone takes the time and has the knowledge to describe an area, on the other hand the article is very narrow. The fundamentals on C-F bonds should go into organofluorine chemistry. Agreed that the artwork is awful as Turnbull mentions. --Smokefoot (talk) 15:11, 22 June 2021 (UTC)

Expert needed

I'd say we clean up the Category:Chemistry articles needing expert attention, which currently has 68 pages and 4 subcategories with 16 pages total. I just did Glass of antimony, for which the concern (lack of accuracy or references) was resolved in 2019; and Blank (solution), which was expanded slightly since the tag was added without explanation. I'll mention William S. Hobson, which survived two AfD's but still has no inline citations or incoming links. I can't add him to List of University of Wisconsin–Madison people due to BLP policy. –LaundryPizza03 (dc̄) 01:01, 3 June 2021 (UTC)

Electrolysis: Not even a tag to begin to locate a rationale. However, there are long-standing concerns on the talk page about factual errors and the article being too narrow in scope. –LaundryPizza03 (dc̄) 01:23, 3 June 2021 (UTC)

Third phase: Unreferenced stub, has not improved since 2006 and didn't even have a stub tag until I replaced the expert tag. –LaundryPizza03 (dc̄) 01:30, 3 June 2021 (UTC)

Stereocenter: The original rationale, by 50.179.252.14 (talk · contribs), read: the article remains, after a long period, as a minimally (lede only) sourced stub, substance of which is not on the level of Eliel or Anslyn (or even Clayden) sources in its depth of understanding, but instead only of watered down Solomons and poorly summarised IUPAC (e.g., see the discussion of the meso case); experts are needed to begin to move this import conceptual article toward being encyclopedic. This rationale was removed in 2018 for being tendentious, the cited talk section does not exist, and the article has improved somewhat, but the article is still rather low on context and references. –LaundryPizza03 (dc̄) 02:04, 3 June 2021 (UTC)

Liquid metal electrode: Unclear, unreferenced stub. Subject does seem to be notable, but content failed verification. PRODding. –LaundryPizza03 (dc̄) 03:06, 3 June 2021 (UTC)

Maybe Dropping mercury electrode and Hanging mercury drop electrode can be merged with it? Neither of those two is tagged as a stub, but they are two variants on a theme and much of each's article is compare/contrast with the other. DMacks (talk) 03:17, 3 June 2021 (UTC)

Agreed; delete LME and merge those two articles under the same title. Actually, the delete step may be entirely unnecessary; what do others think? –LaundryPizza03 (dc̄) 03:53, 3 June 2021 (UTC)

The "American Chemical Society" external-link is doi:10.1021/la0346447, which supports that LME is a general topic (including Hg and others), and that the variation of metal is of scientific interest. Therefore, I'm going to object to the PROD. The merger is an editorial action, and the general LME concept is going to survive...somewhere...so "deletion" as a WP-admin action is not necessary. DMacks (talk) 05:21, 3 June 2021 (UTC)

Fractional coordinates: The issue in question, regarding the validity of one of the equations, has already been resolved. But the article is written like a textbook with few references, and I don't know what to keep. –LaundryPizza03 (dc̄) 04:30, 3 June 2021 (UTC)

nvm, issue resolved except for one cn. –LaundryPizza03 (d

I did some clean-up on the Total Synthesis page and added some sources. Really it is the history and example sections that needs a re-write and should be a collaborative effort if possible. Admitadly, I am a bit too lazy to edit those section. Nevertheless, I got it started Tautomers (talk) 07:13, 26 June 2021 (UTC)

c̄) 04:52, 3 June 2021 (UTC) Ballistic conduction in single-walled carbon nanotubes is a ighly technical that is written like a scientific paper. A lot of the content is unreferenced, so is there original research involved? –LaundryPizza03 (dc̄) 06:48, 6 June 2021 (UTC) Why do so many of the tags seemingly raise concerns about articles being incomplete in coverage? –LaundryPizza03 (dc̄) 07:52, 6 June 2021 (UTC) 34 pages to go! Woohoo! But why isn't anyone else helping? –LaundryPizza03 (dc̄) 08:18, 6 June 2021 (UTC)

Proposed deletion of Donna Amenta

The article Donna Amenta has been proposed for deletion because of the following concern:

Seems to be a rather unremarkable scientist where the wiki page has been in need of citations for 8 years. As the one source provided on this page (which has been the only source since it's inception) is a broken link, this page defacto unsourced. I was unable to find anything meaningful about her through searching methods that could even come close to satisfying notability guidelines. There's also a list of books on the side of the page that she seems to not have written and I am not sure why they are there as they don't even seem science related? Of what I did find, she has an h-score of 5, which is quite terrible, and fails blatently at all WP:PROF guidelines, as well as WP:GNG.

While all constructive contributions to Wikipedia are appreciated, pages may be deleted for any of several reasons.

You may prevent the proposed deletion by removing the {{proposed deletion/dated}} notice, but please explain why in your edit summary or on the article's talk page.

Please consider improving the page to address the issues raised. Removing {{proposed deletion/dated}} will stop the proposed deletion process, but other deletion processes exist. In particular, the speedy deletion process can result in deletion without discussion, and articles for deletion allows discussion to reach consensus for deletion. Heart ^(talk) 04:27, 28 June 2021 (UTC)

How long shall I wait until I remove wrong information?

Per Talk:Heterocyclic_compound#cyclo-Octasulfur, cyclo-Octasulfur is not a compound. However, how long shall I wait for more talks in the Talk:Heterocyclic_compound before I proceed to remove cyclo-Octasulfur from the article page? -- Ktsquare (talk) 15:49, 28 July 2021 (UTC)

You don't need to wait, or ask, to remove information if you believe that it's wrong. If others disagree they'll revert you - and then you must wait until a consensus agreement is reached. --Project Osprey (talk) 16:02, 28 July 2021 (UTC)

If you agree with a proposal for an edit, especially if there is a basis in WP policies or to sync with reliable sources, make the edit:) WP:BOLD is a WP standard. I added a comment supporting it. DMacks (talk) 16:04, 28 July 2021 (UTC)

You waited for over half a year, Ktsquare, when a week or so would have been ample even if you were in doubt. I've now made the change for you, as it was a no-brainer. Mike Turnbull (talk) 16:56, 28 July 2021 (UTC)

On a side note: it breaks my heart that S₈ is not a compound (nor are any of the fullerenes, etc). However several homocyclic sulfur cations are known (S₇²⁺, etc), so those salts qualify.--Smokefoot (talk) 18:41, 28 July 2021 (UTC)

On the other hand, Smokefoot, S₈ or any allotrope of any element are definitely chemical substances (see [1]) and I think that this distinction between compounds and substances is a useful one. Mike Turnbull (talk) 14:40, 29 July 2021 (UTC)

Peer review: Nonmetal

I've listed Nonmetal at WP:Peer review, if anyone could see their way to assist. Thank you, Sandbh (talk) 23:33, 5 August 2021 (UTC)

Chromium(I)

I recently encountered the Phillips selective ethylene trimerisation catalyst (not to be confused with Phillips catalyst), used in the industrial production of linear alpha olefins, particularly 1-hexene or 1-octene. This paper shows it (or its pre-catalyst) to be a rare example of a Chromium(I) compound. As it's industrially important I thought I might list it as an example of Cr(I) at Chromium. However, MDPI papers can be error-filled and I don't really trust their depiction. I haven't looked at metallocenes since undergrad but I'm pretty sure they can't be neutral ligands. A trustworthy source could be doi:10.1016/j.ccr.2010.11.035 but I can't get into it. Could anyone lend an opinion? --Project Osprey (talk) 14:13, 11 August 2021 (UTC)

The CCR review that you cite is very good. I need to read through it to see how definitive the evidence is for Cr(I) as the active species. An old Cr(I) compound is Hein's [Cr(C6H6)2]+ discussed in bis(benzene)chromium. --Smokefoot (talk) 14:58, 11 August 2021 (UTC)

Ionization energy#Exceptions in ionization energies

There are several low quality images that should rather be tables or TeX. Who is able to do the replacements? --Leyo 12:15, 17 August 2021 (UTC)

Hydride anion in aqueous solution

I asked a question related to the stability of the hydride anion in aqueous solution, without resolution, at the Science Reference Desk, here.

The hydride anion in plain water in ambient conditions is unstable.

However, in Pourbaix diagrams for hydrogen in water, the hydride anion H⁻ is shown as a stable species in aqueous acidic solutions (pH 0) at a voltage of ca. less than −2.25. Does this ring true? Sandbh (talk) 04:16, 15 July 2021 (UTC)

Maybe H^- is supposed to exist at highly negative potentials, in some thermodynamic sense, but kinetically it is quenched by H₂O to give H₂ and OH^-. So my guess is that the Pourbaix diagram is more of theoretical interest. --Smokefoot (talk) 14:01, 15 July 2021 (UTC)

• Can you show the diagram? I can't seem to find it. I expect that it's showing the formation of hydride to be thermodynamically favourable under these conditions, which is not the same thing as the hydride being stable. As smokefoot points out, hydride reacts irreversibly with bulk water. Unless we're discussing activity at the double layer? --Project Osprey (talk) 14:50, 15 July 2021 (UTC)

The diagram is on page 114 of this this huge .pdf file. I think that Smokefoot is almost certainly correct that while the thermodynamics may be favourable under some unusual conditions, the kinetics is never favourable. The diagrams were developed in the study of corrosion and I don't see how H⁻ could ever be relevant in real-world situations. Mike Turnbull (talk) 16:59, 15 July 2021 (UTC)

That is quite a tome. I don't see where it shows H⁻ as stable(?) there's 'relative stability' and 'relative predominance' both of which are obviously low. That would stack-up with this being a thermodynamic description. There's also some discussion on pickling embrittlement, so I think this might all be limited to the electrode surface in any event. --Project Osprey (talk) 21:37, 15 July 2021 (UTC)

In Inorganic chemistry (2000, pp. 247−250) and Foundations of inorganic chemistry (2018, pp. 307–310) Wulfsberg gives what he calls redox predominance diagrams for the thermodynamically stable forms of each element up to Z = 102. They are slices of Pourbaix diagrams at pH 0, −3 to 3 V. While the diagrams are for stable species he adds some unstable species shaded in grey. For H in water he shows 3 to 0 V = H⁺; 0 to −2.25 V = H₂; and −2.25 to −3 V = H^–. None of these species have grey shading. Here is a Google Books link to the 2000 text, showing the diagrams for the lighter s and p block elements. Or search GB for "Inorganic chemistry Wulfsberg" and then search in the book for "diagrams of the lighter". That should take you to p. 247. Sandbh (talk) 00:24, 16 July 2021 (UTC)

Interesting... I think the jist there is whether the species is intrinsically stable or not, rather than in solution. Hydride is is a stable form of hydrogen, for instance in sodium hydride, you can keep those hydride ions on a shelf for years. Some species listed in grey are completely unstable like sulfurous acid and some of the others (hydrazine, hydrogen peroxide, chlorate) are highly reactive, so perhaps thermodynamically metastable (although I've never thought off them in quite that way). Others, like carbon monoxide are a bit of a mystery. --Project Osprey (talk) 09:28, 16 July 2021 (UTC)

• Perhaps the redox potential needed to convert CO to CO₂ is less than what's needed to convert C to CO. So you only ever form CO an unstable intermediate? --Project Osprey (talk) 09:41, 16 July 2021 (UTC)

OK, I think that page 253 of the Wulfsberg book explains this best. He points out "If one is carrying out a synthesis or reaction in aqueous solution, water is a potential reactant! ...... Consequently the species of an element under consideration will react rapidly with water and decompose if its predominance range does not overlap the short-term predominance (stability) range of water, -0.6 to +1.8 V." Really, the hydride case is no different than the case of metallic sodium, which has a stability line at -2.71 V (hydride is at -2.25 V in Wulfsberg's diagram). Both metallic sodium and hydride will react instantaneously with the water. On the other hand, in a solvent like dimethyl formamide, hydride (as NaH) is a useful base which only reacts when a weak acid is introduced. Mike Turnbull (talk) 10:33, 16 July 2021 (UTC)

Under the circumstances in question, water is apparently not stable, so will not be present. The form of hydrogen that is stable is the hydride ion.

The remaining conundrum is that if water is not stable and therefore not present in those circumstances, how can the hydride ion be regarded as being present in "aqueous" solution? Sandbh (talk) 03:06, 20 August 2021 (UTC)

NaCl polyhedra

Hi, I hope someone here can help me out as I have nominated this image to become a Featured Picture and now there is some questions about this image.
I hope someone here have the knowledge to provide answers to the questions at this link. The questions are;
1) This representation is different to all the others I've Googled. Does it have Academic authentication?
2) But could you add to the description about which colors are which elements.
I'm a graphic worker and have no knowledge of this subject.
I really hope someone here can help me or tell me someone else who might be able, thanks. --always ping me-- Goran tek-en (talk) 17:18, 23 August 2021 (UTC)

I have got the needed information from another user so this is  Done, thanks. --always ping me-- Goran tek-en (talk) 19:55, 23 August 2021 (UTC)

Should the image could use PyMOL colors for the elements? Is this standard enough (to advise it)? -DePiep (talk) 05:37, 24 August 2021 (UTC)

I will make a new version with those colors so then anyone can use the version they want/need. --always ping me-- Goran tek-en (talk) 10:20, 24 August 2021 (UTC)

Class A assessment for Gold(III) chloride?

Back in July, I did a GA review of Gold(III) chloride, which failed. I just noticed that shortly after that, Keresluna changed the rating of the article to A Class. I'm not an expert as the assessment process, but my understanding is that A class requires a review, and I don't see that such a review was done. Could somebody please take a look at this? -- RoySmith (talk) 14:05, 23 September 2021 (UTC)

@RoySmith:I am sorry, I was not familiar with the process at that time, should I change it back? Keres🌑(talk • ctb) 15:57, 23 September 2021 (UTC)

The process is described at Wikipedia:Content assessment/A-Class criteria. -- RoySmith (talk) 17:34, 23 September 2021 (UTC)

@RoySmith:Should I change it back? Or should I initiate a review? Keres🌑(talk • ctb) 18:27, 23 September 2021 (UTC)

I would start by changing it back. Once you've done that, it's up to you whether you want to start a review. -- RoySmith (talk) 18:34, 23 September 2021 (UTC)

@RoySmith:Changed it back. Keres🌑(talk • ctb) 22:56, 23 September 2021 (UTC)

The Origin of Elements from Carbon to Uranium

Perhaps this extensive reference may be useful for some element and isotope articles?

Kobayashi, Chiaki; et al. (September 15, 2020). "The Origin of Elements from Carbon to Uranium". The Astrophysical Journal. 900 (2). The American Astronomical Society: 33. arXiv:2008.04660. Bibcode:2020ApJ...900..179K. doi:10.3847/1538-4357/abae65. 179.

Thanks. Praemonitus (talk) 04:59, 30 September 2021 (UTC)

IUPAC Goldbook terms/definitions

I've been working with some of the IUPAC people in recent months, to try to find a way to get IUPAC definitions into our chemistry articles in a systematic way - something we've been trying to do since 2007. One problem we've had in recent years was that all IUPAC publications were tagged with copyright information showing licenses that are incompatible with Wikipedia policies. This even led to IUPAC definitions being deleted from articles.

We've worked with IUPAC for the last couple of years to find a solution, and we now have a set of terms/definitions released under a compatible CC-BY-SA license. This was because of concerns that official definitions might be corrupted if the "No-Derivatives" part of a CC-ND license were removed. The solution is that IUPAC has agreed to release all graphical versions of Gold Book terms & definitions under a CC-BY-SA license, and we had this agreement (including a signed letter from the IUPAC leadership) approved by the Wikipedia OTRS folks. If this works out well, it'll probably be extended to all terms & definitions.

So I'm hoping everyone here is supportive of the idea of adding IUPAC terms/definitions into articles where appropriate. This will only affect a limited number of articles, since there is a not a simple 1:1 relationship between articles and IUPAC terms - most articles don't have a corresponding Gold Book entry, and vice versa. But in cases where there is an obvious correspondence between a Gold Book term and an article or article section, I believe it would greatly enhance most articles. In many cases the IUPAC definitions have already been added as text or text boxes - in most cases this was done at a time before copyright limitations were added by IUPAC/DeGruyter.

Assuming people here are supportive of including IUPAC terms/definitions, the question becomes: What is the best format for using these images in articles? I've created a few example formats on my Sandbox page. I'm not sure if direct links from images are allowed in article space - does anyone know? We have thumbnails with linked captions, we have a simple linked image, and we have an image map that can provide links to both the PAC page and the Goldbook page as references. There are of course variations on these - feel free to add other versions to my sandbox page if you have a better one. Your ideas and feedback are most welcome, because we want to get this right, and maybe add it to the MOS if we find a nice consensus. Many thanks, Walkerma (talk) 09:14, 29 September 2021 (UTC)

A valid and useful goal - and it looks like it's taken a lot of back-and-forth to achieve. Well done. My only criticism would be that we only ever hear about these agreement with CAS or IUPAC after they've been finalised, it would be nice to know about what's being done on our behalf. From experience I think most goldbook links are handled by Template:GoldBookRef. If there are going to be hundred of images (and it sounds like there are) then something similar might be a good idea so we only need to enter the correct Goldbook code (e.g. 'M04002' for molecule) to bring up the image. Of course, that's easy for me to suggest, because I won't be the one writing the template. --Project Osprey (talk) 09:44, 29 September 2021 (UTC)

Thanks for your reply. I'm sorry if it seems like a lot of secrecy, but in the case of CAS we were specifically required by CAS to keep quiet during negotiations until their press release came out. In this case (IUPAC), most of the time was spent waiting for IUPAC to get legal advice and get the leadership on board with the idea of a CC-BY-SA license, and no Wikipedians were involved with that. Most recently, I've been the one who's been slow, but just because things got too busy at work for me to focus on it - I can certainly apologize for that. I wanted to get a range of options for this group to discuss. As for the template, yes - we should definitely do that! Thanks, Walkerma (talk) 12:58, 29 September 2021 (UTC)

I agree that it's important to have some authoritative referencing and definitions of key terms, such as from Gold Book. Make your own "gold-standard" joke here {{GoldBookRef|file=...|title=...}} displays the given title as a link to the given file-name on the Gold Book website. It would be easy to have a {{GoldBookDefImage|term=...}} that displays the image of the term's definition along with some standardized caption and/or linking. A standard on Commons is that that images that form a unified set and are used by a template should have a systematic naming pattern. Please consider however that you will likely get MOS pushback for including so much decoration and in-image text beyond the def itself. And that's even if there is MOS/ACCESSIBILITY acceptance of an image-of-text rather than the text itself: CC-BY-SA means replacing it with plain-text is potentially an allowable derivative (see also commons:Category:Images which should not be images, and whether commons might think these are more appropriate on Wikisource). DMacks (talk) 03:38, 4 October 2021 (UTC)

What about ethanoic acid?

IUPAC defs are useful when they are useful. But ...--Smokefoot (talk) 13:38, 29 September 2021 (UTC)

Let's not forget that the Preferred IUPAC name for AcOH is actually acetic acid!

I do know one use for IUPAC names that you might appreciate, though. I worked in the lab at a UK chemical plant for many years, and the guys from the plant were always stealing our acetone wash bottles and net returning them. One smart chemist renamed them with titles like "propanone" or "propan-2-one" or "dimethylketone" and it solved the problem immediately!

These Gold Book terms/definitions, though, are less to do with nomenclature and more to do with more general terms like carboxylic acids. Walkerma (talk) 19:26, 29 September 2021 (UTC)

To your question on linking, Walkerma, Help:Pictures#Links says this may be done and describes how to do it correctly. However I assume that the IUPAC boxes are to be held on Commons so the usual Wikipedia standard should be that clicking on the image takes you first to an enlarged version and then to "more details" which is the Commons page on which the image and its license are stored. I don't see any reason to alter that. So I support the simplest case in your sandbox where the doi for the Gold book is just a standard reference cited in the normal way (with a doi-access=free tag). On the wider question, I support using this IUPAC linking whenever possible, bearing in mind that WP:COMMON will override the IUPAC advice, particularly for article titles. Thanks for your efforts in getting this far. Mike Turnbull (talk) 10:15, 30 September 2021 (UTC)

Thank you for your feedback - that's very helpful! There's a lot of good advice there, which I appreciate, as I'm not as in tune with the nuances of protocol as I once was. I had suspected that we'd probably want to link to a reference, but I wasn't sure how the rules/guidelines have evolved in recent years. Thanks, Walkerma (talk) 17:09, 1 October 2021 (UTC)

I also don't see a reason to modify the standard linking of images to their commons page, on which there would be a link to the website itself. MOS:CREDITS advises not to use the caption to give credit specifically because it is on the file's own page. But a descriptive caption could state that it is the Gold Book def, with a wikilink for Gold Book and a footnote for the ref itself. DMacks (talk) 03:38, 4 October 2021 (UTC)

MfD nomination of Portal:Biochemistry

Portal:Biochemistry, a page that falls under the purview of this project, has been nominated for deletion. Your opinions on the matter are welcome; you may participate in the discussion by adding your comments at Wikipedia:Miscellany for deletion/Portal:Biochemistry (2nd nomination) and please be sure to sign your comments with four tildes (~~~~). You are free to edit the content of Portal:Biochemistry during the discussion but should not remove the miscellany for deletion template from the top of the page; such a removal will not end the deletion discussion. Thank you. North America¹⁰⁰⁰ 07:50, 4 October 2021 (UTC)

List of aqua-ions and their hydroxo- and oxo- derivatives in aqueous solution

​​​​​ I've been working on this list for ca. three weeks, with valuable help from User:Petergans, and a few other WP:ELEM members. When I started I had little idea how it would turn out apart from supposing cations on the left and anions on the right. That is, of course, how it turned out but there were and still are many wrinkles between those two extremes.

Appreciate any observations folks here may have. I intend for it to be eventually listed at WP:FL.

thank you Sandbh (talk) 04:26, 8 August 2021 (UTC)

Is this a synthesis? As there seems to be nothing around outside of Wikipedia called "aqua-ions and their hydroxo- and oxo- derivatives in aqueous solution". Graeme Bartlett (talk) 13:08, 8 August 2021 (UTC)

For chemists, its not very useful. It presents an archaic view of chemistry (what is "HfO²⁺"?). As other editors indicate above and below this remark, its point is slightly unclear although the intent is admirable. One related topic that we could really use is a semi-comprehensive list of polyoxometalates, both homo and hetero.--Smokefoot (talk) 14:21, 8 August 2021 (UTC)

I think this list article has a lot of potential, but why not name it List of aqueous ions or List of aqueous ions by element? The detailed and somewhat convoluted title seems unnecessary and will be confusing to many. The list seems to include other common ions that are not aqua ions or contain oxygen, and in my opinion should do so (e.g., chloride). Since it seems like we don't have a broader, more comprehensive list, why not make this fill that gap? Also, I do not understand the "Combination of species" column. Probably some system I am unfamiliar with, but it is not described in the article that I can tell and many other readers will not understand it either. Mdewman6 (talk) 22:22, 8 August 2021 (UTC)

I agree that the article title is unhelpful, and I think either of your suggestions is superior to the current title and to the previous titles. FYI, the article started out as Periodic table (aqueous chemistry), then change to List of ions in aqueous chemistry, then to List of ions in pure water (aqueous chemistry), then List of stable ions in pure water (aqueous chemistry), and finally to the current title List of aqua-ions and their hydroxo- and oxo- derivatives in aqueous solution. I think your suggestion is so good that I am going to WP:BOLDly move the article.

Second, with regard to the "combination of species" column, it shows how many species (cation, oxycation, anion, oxyanion) a given element forms, and which of the four species it forms. I have added an extended footnote to this effect. Previously the only explanation was the (C), (xC), (A), (xA) located in the other columns, which was inadequate. Does the new addition make it clear? Would the meaning be clearer if the column title was "Number of species"? Or is there some way to improve the wording of the note? Or should the note be better presented using the {{abbr}} template that is normally used to explain an abbreviation like this: "Combinations". Or should a brief explanation be added to the paragraph before the table?

Thank you for your input! YBG (talk) 23:20, 8 August 2021 (UTC)

I now understand the column, but with the description buried as a footnote, I still don't think it is very accessible to most readers and will likely cause confusion. Since it seems simply an attempt to indicate which categories of ions are possible for a given element, isn't that information evident by whether the other columns have entries or not? I think this column should be removed as I feel it's likely just causing confusion rather than conveying useful information. Mdewman6 (talk) 16:19, 10 August 2021 (UTC)

@Mdewman6: You are absolutely correct that this column adds no additional information ... however it does add the capability of sorting by combination of species. As such, it is helpful for editors who wish to keep the periodic table up-to-date. YBG (talk) 00:50, 11 August 2021 (UTC)

@Mdewman6: By the way, it is no longer buried in a footnote, but visible in mouse-over text. Recognizing that the column less important than the other columns, I have moved it to the right of the table. YBG (talk) 06:00, 11 August 2021 (UTC)

I appreciate your help Graeme, Smokefoot, and Mdewman6.

Much information about which ions the elements form in water can be found in Schweitzer & Pesterfield 2010, The Aqueous Chemistry of the Elements. I say "much", as they sometimes abstract the species concerned. Sometimes they discuss what ions are involved in the abstraction, sometimes not. Consultation of the sources used by them, or sources such as Baes & Mesmer 1976, The Hydrolysis of Cations (which User:Petergans mentioned) or Brown 2016, Hydrolysis of Metal Ions, allows the unpacking of such abstractions.

On utility or being archaic, there is an evident periodic table pattern to the occurence of the ions concerned. Thus:

"Professional academic resources have begun to encourage an examination of periodicity with activities based on pattern recognition of element properties, the fundamental concept Mendeleev and Meyer used in the 19th century to create the first PTE"

— Bierenstiel M & Snow K 2019, "Periodic universe: A teaching model for understanding the periodic table of the elements", Journal of Chemical Education 96 (7), 1367–1376 (1367), doi:10.1021/acs.jchemed.8b00740

On HfO²⁺, S&P say about the Zr equivalent, "This formula is a simplification of the tetramic species that is believed to predominate, namely Zr
₄(OH)⁸⁺
₄." If that is the case for HfO²⁺, they do not say.

Petergans has been adding polyoxometalate species.

Aside from chlorine species there are no other species with chlorine in them, that I can see. Sandbh (talk) 03:38, 9 August 2021 (UTC)

There is a fundamental issue with this article: the establishment of which species exist in aqueous solution over a wide range of pH is based on computer modelling, see #model selection in Determination of equilibrium constants​. This is compounded by the fact that equilibrium with polymeric species is often reached rather slowly. A guide to model selection is provided by known structures of species that have been precipitated from solution, but it does not follow that those are the major species that are present in solution. Also, there may be ambiguity as in the empirical formulae of HfO²⁺ or Hf(OH)₂²⁺ which cannot be resolved for the presumably tetrameric species in solution. In my edits I have omitted those species whose existence in solution is most doubtful. Petergans (talk) 08:02, 9 August 2021 (UTC)

Many of the Cation species are not present as a bare metal ion in solution, but will be present as a hexaaqua complex. The colour depends on that octahedral arrangement of water molecules. eg Ni(H₂O)₆²⁺ Graeme Bartlett (talk) 12:54, 9 August 2021 (UTC)

No stable oxyanion is given for hydrogen, is it not hydroxide? …and hydroperoxide, etc --Project Osprey (talk) 13:50, 9 August 2021 (UTC)

I think that the project is way too ambitious. And to do it right, one needs to be very familiar with metal ions in aqueous solution, rare knowledge. As Petergans points out, pH is a huge factor. Olation can be slow. 17O NMR studies show that even "simple stuff' like hydrated nickel halides and sulfates are partially associated. One approach would be to take on one important metal, say Zn2+, and nail it. I have been considering writing an article transition metal hydroxide complexes (vs just transition metal hydroxides) but most of the article would be on mixed ligand species like [Co(NH3)5OH]++ because few homoleptics exist. Also reviews on the topic are few.--Smokefoot (talk) 14:33, 9 August 2021 (UTC)

I agree that this page is ambitious, as the topic of aqueous speciation, ions, and complexes cover entire textbooks and is a function of pH, complex equilibria, and solution composition, and here we are trying to reduce it essentially to one table. But, I think it can be made clear that this article is not comprehensive nor complete, but instead is a compilation of the major ions for each element, with many links to WP articles. I don't think we need to get bogged down in pH-dependent equilibria and such here, that can be fleshed out in articles for specific ions as appropriate. Mdewman6 (talk) 16:19, 10 August 2021 (UTC)

Thank you@Mdewman6: that was my intent for the article. There are several monographs that give this information. But one has to have one's wits about oneself, as user:Petergans has intimated, and mention on what basis the authors of RS are making their claims. That was the purpose of the notes column, among other things, until it was removed for some reason. I supposed this could be done via footnotes instead.

I was interested to see what the periodic table distribution would be for these species. This is mapped in the accompanying periodic table but I haven't checked to see if it's still accurate since recent amendments to this list, some of which I intend to contest, in due course.

user:Petergans added the text accompanying the list (to whom, thank you!). This text needs some work as I feel parts of it are unintelligible to the general reader.

If things go as intended I'll post periodic updates to this talk page. Sandbh (talk) 06:16, 6 October 2021 (UTC)

Courtesy ping@Petergans: Sandbh (talk) 08:54, 6 October 2021 (UTC)

Requested move: Lists of IARC agents

An editor has requested for List of IARC Group 1 Agents - Carcinogenic to humans to be moved to IARC Group 1. Since you had some involvement with List of IARC Group 1 Agents - Carcinogenic to humans, you might want to participate in the move discussion (if you have not already done so).

An editor has requested for List of IARC Group 2A Agents - Probably carcinogenic to humans to be moved to IARC Group 2A. Since you had some involvement with List of IARC Group 2A Agents - Probably carcinogenic to humans, you might want to participate in the move discussion (if you have not already done so).

An editor has requested for List of IARC Group 2B Agents - Possibly carcinogenic to humans to be moved to IARC Group 2B. Since you had some involvement with List of IARC Group 2B Agents - Possibly carcinogenic to humans, you might want to participate in the move discussion (if you have not already done so).

An editor has requested for List of IARC Group 3 Agents - Not classifiable as to its carcinogenicity to humans to be moved to IARC Group 3. Since you had some involvement with List of IARC Group 3 Agents - Not classifiable as to its carcinogenicity to humans, you might want to participate in the move discussion (if you have not already done so). Havelock Jones (talk) 21:52, 6 November 2021 (UTC)

Wiki Science Competition 2021

Hi, I'd like to remind you all that Wiki Science Competition 2021 has started in many territories last week. It will last until November 30th or December 15th, depending on the areas.

WSC is organized every two years, and people from all countries can upload files (the goal are the international prizes) but specific national pages are also set up, for example for USA or Ireland. These national competitions (when they exist) act as an additional incentive to participate.

We expect a sitenotice to show up for all readers here on enWikipedia as well, but probably during the second half of the month when all countries with national competitions are open for submission. In the meantime, if you are planing to upload some nice image or video to Commons, please consider to submit them using the WSC interface, you might win a prize.--Alexmar983 (talk) 01:07, 9 November 2021 (UTC)

Nonmetal at FAC

I'd be grateful if anyone here has the interest and time to look at this one. Thank you, Sandbh (talk) 00:39, 11 October 2021 (UTC)

After two unsuccessful nominations, round 3 at FAC is here. Sandbh (talk) 00:49, 31 October 2021 (UTC)

The FAC has now rec'd its first Support. Is there anyone here who could assist? Sandbh (talk) 02:31, 14 November 2021 (UTC)

Structure diagram service?

Is there a service for producing high-quality structure diagrams, in the same spirit as Wikipedia:Graphics Lab/Map workshop? I'm doing a GA review of Riboflavin, which has some structure diagrams that are of such a low quality, they're nearly unusable. I imagine somebody who's a ChemDraw wiz could come up with high quality replacements pretty quickly. -- RoySmith (talk) 20:53, 18 November 2021 (UTC)

I can't currently help with new images, but the existing images look to have been made by badly editing File:Riboflavin Synthase Mechanism.png --Project Osprey (talk) 23:44, 18 November 2021 (UTC)

Maybe: https://www.cheminfo.org/wikipedia/ ? (no experience myself). -DePiep (talk) 11:53, 19 November 2021 (UTC)

I'd be happy to ChemDraw some images. We have Wikipedia:WikiProject Chemistry/Image Request, but nobody seems to use it lately. There are some tags on commons if you find a mistake or a low-quality image there, but those categories are large and again nobody is actively working through them. Probably best to just make a one-off request here or on a user-talkpage of a participany you know or that seems active if you have a specific need. DMacks (talk) 23:00, 19 November 2021 (UTC)

Cool, thanks. Foolish me thinks that you could just copy-paste the SMILES code from the article into some appropriate piece of software and out pops a perfect image, but I don't suppose it's quite that easy? -- RoySmith (talk) 23:13, 19 November 2021 (UTC)

Chemdraw can do that SMILES→PIC, but it does have limits, where it makes a mess. And my version does not make .svg files. Graeme Bartlett (talk) 03:16, 20 November 2021 (UTC)

Same with mine. I have no idea why...SVG on Mac has been widely supported for many years in general, but CD on that platform tends to lag in several ways. There are some online and some open-source programs that can do it. But in all cases, they make arbitrary choices about lots of layout/orientation details that might not match or make sense in the context of an existing article with multiple images (same as any machine translation). DMacks (talk) 05:08, 20 November 2021 (UTC)

I am very familiar with chemical drawing packages, which I've used since the 1980s, and can turn their output into .svg files of compact size. If RoySmith or anyone else makes a specific request on my Talk Page, I'd be happy to oblige. My recent efforts include those at molnupiravir and PF-07321332. There are some software packages that can give reasonable .png from molfiles (in turn available from Chemspider as downloads) but for fidelity the stereochemistry etc. really needs the attention of an organic chemist. Mike Turnbull (talk) 16:57, 20 November 2021 (UTC)

Template chembox - Lua and infoboxes

Hello! In the recent days I've been discussing about {{chembox}} in regard to changing its technical infrastructure to be rewritten in Lua so that we won't need tens of subtemplates to make use of its modular design. The discussion is currently happening here where the reasons for the proposed change are also discussed. It was suggested to me to also notify here so I'd appreciate any kind of feedback. Please make sure to comment there so we can have 1 single discussion for the topic. - Klein Muçi (talk) 12:27, 19 November 2021 (UTC)

To be clear: at Talk:Chembox § Convert Chembox into Lua module, Klein Muçi proposes to allow {{Chembox}} be changed into a Lua-based {{Infobox}}. -DePiep (talk) 20:53, 21 November 2021 (UTC)

Talk:Alchemy#RFC: Should Alchemy be included in Category:Pseudoscience

People here may want to opine there. Headbomb {t · c · p · b} 18:50, 12 December 2021 (UTC)

Template:Chembox has an RFC

Template:Chembox has an RFC for possible consensus. A discussion is taking place. If you would like to participate in the discussion, you are invited to add your comments on the discussion page. Thank you. DePiep (talk) 15:01, 16 December 2021 (UTC)

Chembox: proposal to remove unspecific data

• See Chembox § Supplementary data page: link rows to remove, about removing non-specific/non-data rows & links (eg, remove link [[Ammonia (data page) § Spectral data]] from infobox Ammonia). If interested, please take a look there. -DePiep (talk) 06:52, 18 December 2021 (UTC)

Recurring issue with articles on organic chemistry

Here is a typical article on an (important) organic reaction: "The Sharpless epoxidation reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols.<ref name="Katsuki1980">{{cite journal|author=Katsuki, T.|author2=[[K. Barry Sharpless]] |journal=[[J. Am. Chem. Soc.]]|year=1980|volume=102|pages= 5974| doi=10.1021/ja00538a077|title=The first practical method for asymmetric epoxidation|issue=18}}</ref><ref>{{cite journal|authors=Hill, J. G.; Sharpless, K. B.; Exon, C. M.; Regenye, R.|journal=[[Org. Synth.]]|volume=63|pages=66|year=1985|doi=10.15227/orgsyn.063.0066| title=Enantioselective Epoxidation Of Allylic Alcohols: (2s,3s)-3-propyloxiranemethanol}}</ref>

Notice that the references might be of some historical interest since they cite the discovery. Our readers are not visiting this article to learn history (i.e., worship at the altar of organic chemistry), readers are here for information on a reaction: how its done, state of the art, overview. So in general, we should reconsider this style of writing and emphasize reviews/books in the lede. The history can be put elsewhere in the article. My 2 cents.--Smokefoot (talk) 13:43, 16 December 2021 (UTC)

The lead is a summary of the article and should not (normally) have any references at all. I can't see any problem with a historic section in the article, and a (short) summary in the lead Christian75 (talk) 16:09, 25 December 2021 (UTC)

Good point. I was referring to many articles on traditional organic synthesis where the lede exclusively references discovery papers. I agree that discovery and history are often desirable content, but my concern is that if we have refs in the lede, they should be to contemporary overviews. Example, when looking up older versions of the [epoxidation], the original publications by Sharpless et al. were cited in the lede. These refs do not offer perspective and are generally obsolete in terms of methodology. Some of our pioneering editors in the organic area, e.g., user:~K, tended to pay homage to discovery vs citing broader sources. My 2cents only. --Smokefoot (talk) 16:53, 25 December 2021 (UTC)

Please look at [case] on the Claisen rearrangement.--Smokefoot (talk) 00:34, 27 December 2021 (UTC)

@Smokefoot: These references should be in relation to the name of these name-reactions. The top sentence in itself does not need these references, it would be better to replace them on this sentence with some high-level recent reviews, focusing on the subject (or leaving out references altogether, they will come in the rest of the article). Paying homage, which for name-reactions is something that belongs in the lede anyway, can then be done with 'The reaction was named after XXX (and YYY) for ZZZ<ref>...</ref>', where these two references then can be used. The history section (which is educational for interested readers - how science progresses) can then elaborate on the 'invention' and progress through time. --Dirk Beetstra ^{T C} 11:01, 27 December 2021 (UTC)

Request for CCDC identifier in chemical-related infoboxes

Chemicals with crystal structures have their CCDC numbers. The CCDC number is an identifier for a single crystal structure per the Cambridge Crystallographic Data Centre. See also P6852 (Wikidata). --Leiem (talk) 13:26, 27 December 2021 (UTC)

One issue with that suggestion is that CCDC numbers are not single-valued per chemical. For example (at an extreme!) 5-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile has at least 13 IDs listed here. Many chemicals, of course, have no CCDC number at all. Mike Turnbull (talk) 15:05, 27 December 2021 (UTC)

At WD: [2] (talk:P6852 (Wikidata): not that extreme, max=5, mostly 1. What could the list look like in chembox? wikilink(s), tiny image(s)? -DePiep (talk) 15:41, 27 December 2021 (UTC)

... or add another EL like Tris(acetylacetonato)iron(III) → [3]? -DePiep (talk) 16:02, 27 December 2021 (UTC)

Thinking about this, we already have in Template:Chembox Structure these entries : | Structure_ref = | CrystalStruct = | SpaceGroup = etc.

Would it not be better to create a new template called {{CCDC}} which would automatically generate the correct citation when supplied with the CCDC number? Then this could be the value at Structure_ref and would remain consistent with other existing Chemboxes. We do something similar with our template {{PPDB}} which links to entries in the pesticides properties database. Multiple entries would even be consistent with this approach, just by reusing the template or allowing it to take multiple values. Mike Turnbull (talk) 16:54, 27 December 2021 (UTC)

Good plan. First re {{Chembox}} solutions: better not spend too much energy on this. Even if {{Chembox}} were more flex by being Lua module (is projected), then the same issue plays: not enough space, too many datapoints, lots of non-infobox info there. A "single" data row could be added always, but in the longer term we need to change the infobox drastically.

Then, about a dedicated template {{CCDC}}: it could also pull its data from wikidata (with smart handling, option local overwrite, etc). Chembox already does this with E number, ECHA InfoCard ID, DTXSID (CompTox Chemicals Dashboard) (more here).

Third, about out-of-the-chembox solutions: {{PPDB}} (~160 tc's), for example in Urea § External links, is a good start. For a few years, I am pondering to add section ==Data sheet== to chemical articles, where there is enough space & reason to have lots of data (graphs, lists, ExternalLinks, merged separate data pages). That too could be automated (a big template, organising much data & graphics, like a Chembox let loose). -DePiep (talk) 17:17, 27 December 2021 (UTC)

@DePiep: this is pretty much what I suggest with the discussion on the datapages now. This is too much, and too specialized to be in an infobox. On Ice we say "Ice may be any one of the 19 (Metcalfe, Tom (9 March 2021). "Exotic crystals of 'ice 19' discovered". Live Science.) known solid crystalline phases of water, or in an amorphous solid state at various densities." .. now is ice in itself notable enough, but solid structure of 5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile is never going to get anywhere, it is far beyond an encyclopedia to discuss those here. Datapages there serve a function, with a 'chembox let loose' or another structured way of displaying data that is 'too specialized' to put on the mainpage, but where either the data is of interest or where a short discussion of the fact (I can imagine that it could be interesting to read that there are 13 known structures of 5-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile and 'why' (in fact). Dirk Beetstra ^{T C} 07:39, 2 January 2022 (UTC)

@Beetstra: You're right in data that must be available. Minor diffs about solution (say, page & layout).

First, about {{PPDB}}: this give some external ID+link only. Not fit for article body. (That template is quite ugly & bad btw, like formatting & sourcing). At least it should show the external ID (as CASRN does in IB Chembox). Projected {{CCDC}} could do the same (provided: database is OK, good formatting & showing, etc.).

Also, as I say elsewhere today, I think dedicated article section ==Data sheet== is a good place to add data. Only huge data sheets should fork into a separate page (water). Likely this section is structured (less verbose), can handle all chemical data, can be automated & use formatting templates, like an infobox let loose, can unload IB Chembox (halve its content :-) ). -DePiep (talk) 09:41, 2 January 2022 (UTC)

That is also an approach. Start with a ==Data sheet== section, and if that starts taking about 10-20% of article length, then split it out into a dedicated datapage. Dirk Beetstra ^{T C} 11:00, 2 January 2022 (UTC)

:-) Growing size is best indicator for forking into a DP. Article quality required anyway. -DePiep (talk) 11:11, 2 January 2022 (UTC)

But there is also no problem with just skipping the step - populate a DP directly from the infobox, and delete the data from the infobox which is 'excessive' (vapour pressures at 20 different temperatures, leave only RT; solubility in water at 10 different temperatures, leave only RT). -- Dirk Beetstra ^{T C} 13:30, 2 January 2022 (UTC)

Some external criticism

Here's an external peer review of some of our pages doi:10.1080/87567555.2021.2004387. Can't get into it myself, but the abstract seems fairly withering. Their advice: don't bother reading beyond the first paragraph. I'll confess to being curious about the contents. They cite that paper from a few years back which took aim at our images doi:10.1021/acs.jchemed.6b00478. Merry Christmas everyone. --Project Osprey (talk) 22:57, 24 December 2021 (UTC)

In any case, the paper looked at these Chem articles (and similar number of articles in other STEM fields):

• Relative atomic mass rated as "Suitable for opportunistic learning when supplemented with authoritative resources"
• Oxidation state rated as "Not suitable for opportunistic learning"
• VSEPR Theory rated as "Recommended for opportunistic learning"
• Intermolecular forces rated as "Suitable for opportunistic learning when supplemented with authoritative resources"

The article concludes with these points:

• "...STEM articles in Wikipedia cannot be recommended as useful resources for opportunistic learning. Some articles over 15 years old with thousands of editors still contain errors. ..." (memo to self: remember to remove errors from Wikipedia).
• "Perhaps due to the large number of editors who tend to add rather than remove words, shallow and broad overviews of topics were often given..."
• "In contrast, some text was dense with terminology..."
• "Articles commonly lacked conceptual development..."
• "For STEM articles, sometimes the first paragraph is as good as it gets."

They also cite this article published on the WWW https://www.researchgate.net/publication/200772541_Power_of_the_Few_vs_Wisdom_of_the_Crowd_Wikipedia_and_the_Rise_of_the_Bourgeoisie#fullTextFileContent, which contends that early on (<2005) Wikipedia was written by experts but now is mainly written by lower level editors.

Merry Christmas to our happy band of bourgeoisie editors.--Smokefoot (talk) 04:09, 25 December 2021 (UTC)

What is Opportunistic learning, and how does it relate to an encyclopedia? BTW, is this O.L. done by desktop or by mobile? Because, in mobile my infoboxes are in paragraph #2 :-( -DePiep (talk) 04:27, 25 December 2021 (UTC)

O.L. = "informal, self-regulated study to learn, relearn, or be introduced to a concept. This contradicts Wikipedia’s stated purpose as “not an instruction manual, guidebook, or textbook”. O.L., I think, means self-motivated browsing, which leads to learning.--Smokefoot (talk) 12:47, 25 December 2021 (UTC)

OK, so the damage we're building is limited. OTOH, browsing a paper encyclopedia, exactly that way, is how I prepared for wiki tbh. Have nice festivities for you too, my fellow bourgeois elite editors, DePiep (talk) 14:38, 25 December 2021 (UTC).

• It's now found it's way onto the Signpost (not by my hand). There's some additional discussion there for those that are interested. --Project Osprey (talk) 21:07, 2 January 2022 (UTC)

Methanediol article probably needs updating

I haven't read the paper yet but it looks like the article for Methanediol probably needs to be updated, as it appears that it has been synthesized in pure form. See [4] and specifically [5]. I'm posting it here because otherwise I will certainly forget about it. BirdValiant (talk) 03:21, 3 January 2022 (UTC)

Help needed

Wonder if there is a solution to these these templatestyles stripmarker in. I posted a message to BrownHairedGirl who suggested, ...since there are 111 pages with this problem, some remedy is needed. I suggest that you ask at WT:CHEM?
Can this be fixed and how remedy in the future? Thank you for your time. Lotje (talk) 06:37, 30 December 2021 (UTC)

The problem seems to be that the template (for example {{chem2}}) is specifically NOT supposed to be used in citations — see template documentation page. In ordinary text, use of that template turns CO2 into CO₂, in other words it adds subscripts to the text that would otherwise render without it. You can of course use alternative _and tags to achieve CO₂ and that works everywhere (look at my source code to see the difference). Some pages with the problem, for example Carbon capture and storage show the error literally dozens of times, which leads me to suspect that at an earlier time the problem didn't exist since I would have thought that the editors working on that page would have noticed and commented! One laborious method to fix this will be to use your search and go through all the hits fixing them one-by-one. Before resorting to that, I suggest we ask DePiep to give it consideration, as our template expert. Mike Turnbull (talk) 12:03, 30 December 2021 (UTC)

The #Test below shows, it is {{Chem2}}. Not checked (yet) if its this cause in all 111 issues. As note, {{Chem2}} should not be used in <ref>s. Ever. I am not aware of a solution (todo: is plain <sub>/<sup> viable?). -DePiep (talk) 14:45, 30 December 2021 (UTC)

test

From Tellurate#TeO4−5_ion, current ref#12:

DEMO01 ... as in Li₄TeO₅ and TEST01Ag₄TeO₅

DEMO02 ... remove Chem2 altogether: TEST02-Ag₄TeO₅

DEMO03: Chem2 expanded:

 <span class="chemf nowrap">Ag<sub class="template-chem2-sub">2</sub>Te<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">6</sub></span>

-DePiep (talk) 14:41, 30 December 2021 (UTC), -DePiep (talk) 16:12, 30 December 2021 (UTC)

DEMO04 Yes, I think so, although tedious to create, as TEST04 here

References

Cleanout by replacement in ref (Chem2 into sub/sup)

The last time we had global changes to make, Project Osprey and I did them by hand, with one of us starting a the top of the search and the other from the bottom, until we met in the middle. I'd be willing to do this if other(s) helped: 111 is not too bad and most articles only have a limited number of instances. Mike Turnbull (talk) 15:25, 30 December 2021 (UTC)

• Sorry, I've not been here much over Christmas and this discussion now has many sub-sections. Is there still something you need me to do? --Project Osprey (talk) 21:03, 2 January 2022 (UTC)

Many of these appear to be due to the {{CO2}} template calling Chem2. I propose rewriting it to {{nowrap|{{#if:{{{link|}}}|[[Carbon dioxide|CO₂]]|[[CO₂]]}}}}<noinclude>{{Documentation}}</noinclude> ---does that look correct? Graeme Bartlett (talk) 20:54, 30 December 2021 (UTC)

Graeme Bartlett Your solution would work but (I think) leave the references without their subscript 2. So I suggest that rather than alter the {{CO2}} template, we go through the articles from the search provided by Lotje and make the fixes in a more robust way, using super/subscripts. I see you have started to do this and I have also begun. Anyone can chip in by re-running the search until it gives zero hits. Mike Turnbull (talk) 11:50, 31 December 2021 (UTC)

@Michael D. Turnbull: is Space-based measurements of carbon dioxide correct now? Thanks for taking a closer look to see if it is okay now. Thank you for your time. Lotje (talk) 12:11, 31 December 2021 (UTC)

@Lotje: Yes, seems perfect. The templatestyles stripmarker in warnings in the references have all gone and you'll notice that the hidden category "CS1 errors: invisible characters" has disappeared from your revision (if you have the hidden categories visible through your preferences). Thanks for helping to sort this out. Mike Turnbull (talk) 16:45, 31 December 2021 (UTC)

Glad I could be of any help. Lotje (talk) 16:49, 31 December 2021 (UTC)

I cleaned out the last 4 this morning. Happy New Year every one! Graeme Bartlett (talk) 21:20, 31 December 2021 (UTC)

And in all this discussion, no-one thought to advertise this at {{CO2}} or any of the other related templates? The first I heard of this was that a massive number of articles I watch suddenly had the template replaced with their HTML equivalent. Even worse, it wasn't just the few places where there was a conflict with the {{cite}} family of templates but wholesale removal. This is a bad way to do business.

At User_talk:Graeme_Bartlett#Stripmarker_error, GM says that he dislikes the {{chem}} family of templates and replaces them whenever he can with HTML equivalents. I am of the opposite opinion and dislike HTML mark-up in what is suppose to be wiki mark-up. Using HTML mark-up in wiki pages is promoting form over function. Templates allow us to globally adjust how we display such things without having to tediously search and replace. It also allows us to add future features like links, tooltips, etc without having to go on awkward search and replace missions. If the chem series of templates have a problem, then we fix the problem at the source. If chem can't/won't be fixed, then the next solution to look at is to simply use the HTML constructs within the CO2 and similar templates. Easier then the search and destroy mission currently under way. Also easier to undo when the root problem is fixed. And far less disturbing to hundreds of articles.  Stepho  talk  21:16, 1 January 2022 (UTC)

The main reason for my dislike, is because on my browser when I do ctrl-F to search for a chemical formula, it does not find it when formatted with chem or chem2. This can probably be fixed in those templates as mentioned above. What I understand is it is something to do with how to get superscripts positioned directly above subscripts. And if this is fixed, it may well work in citations as well. Graeme Bartlett (talk) 21:46, 1 January 2022 (UTC)

Can you give an example of how you search for a chemical formula?

I'm not sure of the exact details of the problem but I'm willing to help look for a solution. Here are a few ways to display superscripts above subscripts.

method	mark-up	result
CSS	<div style="display:inline-block;vertical-align:middle;margin:0 0.2em 0.4ex;text-align:right;"><span><sup style="display:block">14</sup></span><span><sub style="display:block">6</sub></span></div>C	146 C
{{su}}	{{su|p=14|b=6|a=r}}C	14 6C
{{chem}}	{{chem|14|6|C}}	14 6C
{{nuclide}}	{{nuclide|C|14|bl=6}}	14 6C

There are, of course, more ways. nuclide and chem use su to do the super/subscripts. But it might be something else in chem that is triggering the problem in cite.

Does anybody use chem directly in cites or just indirectly through CO2 and similar? The simplest solution may be to make {{CO2}} just use CO₂ and similar for {{NOx}} and others. It would loose some flexibility for general prose (limits future features mentioned above) but simplifies use in cites.  Stepho  talk  00:12, 2 January 2022 (UTC)

Testing what triggers the cite warning:

method	mark-up	result
HTML	{{cite |title=CO<sub>2</sub>}}	CO2
{{su}}	{{cite |title=CO{{su|b=2}}}}	CO 2
{{chem}}	{{cite |title={{chem|C|O|2}}}}	CO 2
{{chem2}}	{{cite |title={{chem2|CO2}}}}	CO2 {{citation}}: templatestyles stripmarker in |title= at position 1 (help)
{{CO2}} (chem2)	{{cite |title={{CO2}}}}	CO2
{{CO2}} (chem)	{{cite |title={{CO2/sandbox}}}}	CO2

Which shows that it is the module chem2 that triggers it, not the chem template. So, simple solution could be to change the CO2 template to use chem.

GB: we can work on the search and number stacking as separate issues from the cite problem.  Stepho  talk  03:12, 2 January 2022 (UTC)

Now it looks like search is working for chem2, but not for chem. SO thanks to those that rectified that. Graeme Bartlett (talk) 20:32, 2 January 2022 (UTC)

Some time recently I converted a bunch of sub/super scripts to {{chem}} and then I discovered {{chem2}} which I found to be significantly superior. You've added yet another reason to prefer chem2 to chem. YBG (talk) 02:51, 3 January 2022 (UTC)

A friendly administrator has converted {{CO2}} from chem2 back to chem, as per my request. This removes the conflict with the cite family of templates.  Stepho  talk  21:34, 3 January 2022 (UTC)

Alcohol: disambiguating links

Hi. Alcohol is now a disambiguation page as the result of an RM, and at this point several hundred links to it still need to be disambiguated. Most are straightforward, but there are also some for which it isn't clear, at least to a layperson, whether the general class of chemicals is meant or ethanol specifically. Any help is appreciated! Lennart97 (talk) 15:58, 6 January 2022 (UTC)

For those interested: the RM ("per WP:DAB: there is no primary topic between drug and chemical"), & the resulting moves

• Alcohol → Alcohol (chemistry)
• Alcohol (disambiguation) → Alcohol
• Alcohol (drug) unchanged

-DePiep (talk) 17:02, 6 January 2022 (UTC)

We're now down to "only" a few thousand links to "Alcohol", or only 800–900ish from article-space. Those who were proponents of this move should take it upon themselves to spend the time to learn about and act on what they proposed. The amount of time and effort needed to clean up after fairly innocuous usage should have been raised in that RM (it's been a salient objection in at least one other recent one). DABresolver isn't working for me (won't let me submit my changes). DMacks (talk) 17:20, 6 January 2022 (UTC)

Is it worth a move review? If there was no consensus, and there was not consensus against the status quo, then the result should have been not moved. Mdewman6 (talk) 18:08, 6 January 2022 (UTC)

Looks like a good close to me; no consensus on what the primary topic is means there is no primary topic. The links I've fixed so far in any case seem to confirm this, as many are indeed intended for alcohol (drug).

For anyone who wants to help clean up, I advise DisamAssist, which works very efficiently in cases like this. Lennart97 (talk) 18:33, 6 January 2022 (UTC)

ehm, DA has no save-button. Clicking "change" changes the wikitext .. and saves it right away. No visual feedback ... Is this legal? (let's RTFM oh wait). -DePiep (talk) 19:49, 6 January 2022 (UTC)

Yes, I think it is. Be careful though; I don't think alcohol here refers to the general class of compounds, but rather to the drug. Lennart97 (talk) 20:03, 6 January 2022 (UTC)

@DePiep: one more note on DA usage: the "intentional link to DAB" option creates a link to Alcohol (disambiguation), which redirects to Alcohol, per WP:INTDAB. This is for intentional links to a disambiguation page in articles. However, redirects such as Alchohol should redirect to the dabpage directly, since otherwise you get a double redirect. So in DA, redirects should be skipped instead. Lennart97 (talk) 20:13, 6 January 2022 (UTC)

Enough. No use in others having to check my edits. If only there were a DA guide. -DePiep (talk) 20:16, 6 January 2022 (UTC)

Thanks for your help. I noticed the one article and a redirect, but otherwise had and have no intention of checking your edits. I think the INTDAB/redirect thing is the only thing missing from the usage guide really, and since the creator doesn't seem to be active I'll see if I can add it. DABsolver, by the way, is an alternative which is less efficient but possibly more user-friendly. Lennart97 (talk) 20:30, 6 January 2022 (UTC)

On a mostly unrelated note, but since I'm here anyway, is Pyranol a notable topic? Lennart97 (talk) 20:32, 6 January 2022 (UTC)

Not only not notable but with no sources, no incoming links and hardly any views. Can you remind me how we get rid of such junk, Lennart97? Mike Turnbull (talk) 10:26, 7 January 2022 (UTC)

So, I have WP:PRODed it. Mike Turnbull (talk) 10:35, 7 January 2022 (UTC)

Yes, PROD is the way to go :) Lennart97 (talk) 10:42, 7 January 2022 (UTC)

In this case, checking me (as in 'following me editing') was useful, I got four or five reverts. That tools is like irresponsible. And no, I dunno about pyranolor chemicals. That's just an attitude I choose to meet interesting people. -DePiep (talk) 20:59, 6 January 2022 (UTC)

Only 14 links left. (And a big thanks to Mike Turnbull for fixing over 250 of them today). Lennart97 (talk) 17:09, 7 January 2022 (UTC)

All  Done. there may be some where others would disagree with my choice of disambiguation but I doubt anyone will check (or care ;-) Mike Turnbull (talk) 18:04, 7 January 2022 (UTC)

Only Piperine still has one. Is that alcohol (chemistry) or ethanol? Lennart97 (talk) 19:32, 7 January 2022 (UTC)

Without a source, I have removed the relevant data figure. –LaundryPizza03 (dc̄) 05:58, 8 January 2022 (UTC)

Rfc about the periodic table in the lede of the PT article: 18 columns or 32?

Should the periodic table in the lede of the periodic table article have 18-columns or 32?

The rfc is here. Sandbh (talk) 22:12, 20 January 2022 (UTC)

TFA nomination for Synthetic diamond

I have nominated Synthetic diamond to run as today's featured article for an unspecified date. Please join the discussion by clicking here. Z1720 (talk) 19:21, 23 January 2022 (UTC)

Invitation to discussion: FAC 4 nomination of nonmetal

Please accept this note as an invitation to participate in the discussion of this latest FAC nomination for the nonmetal article.

Thank you. Sandbh (talk) 07:25, 4 February 2022 (UTC)

Invite to GAR of nonmetal

Nonmetal has been nominated for an individual 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. CactiStaccingCrane (talk) 16:19, 9 February 2022 (UTC)

The page you linked to was the GA1 review of 2013. Is that what you intended, CactiStaccingCrane? Mike Turnbull (talk) 17:29, 9 February 2022 (UTC)

FYI

For anyone interested, the potential review was withdrawn at Talk:Nonmetal/GA2. Mike Turnbull (talk) 12:31, 10 February 2022 (UTC)

Source for Edit to Chemical Equation Page

I am looking for a source for a statement I know is true but need to verify: Chemical equations does not provide information about the reaction rate or the reaction pathway which is important in biochemistry. I would like some help finding a reliable source for this statement. ScientistBuilder (talk) 17:12, 15 February 2022 (UTC)

New colorlized ChemDraw

illustration of highlighted chemdraw

Just so folks are prepared for more colorful images, the newer versions of ChemDraw have "highlighting" features. We are already accustomed to colorized ChemDraw and related chemical drawing software, which is employed pretty selectively.

I cannot at this moment foresee any reason we would recommend the highlight feature (or stated differently: we might recommend against use of this feature except on rare occasion). --Smokefoot (talk) 14:17, 16 February 2022 (UTC)

I had occasion to use coloring recently to highlight rearrangement reactions for 5-aminoimidazole ribotide, currently awaiting a "DYK". I use Biovia Draw / Inkscape but the result is similar and very useful for this sort of diagram. Mike Turnbull (talk) 16:39, 16 February 2022 (UTC)

Nice example and an amazing conversion. --Smokefoot (talk) 18:23, 16 February 2022 (UTC)

Cyclol Featured article review

Cyclol has been nominated for a featured article review here (largely due to uncited paragraphs). Please join the discussion on whether this article meets 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" the article's featured status. The instructions for the review process are here. T.Shafee(Evo&Evo)^talk 00:18, 9 March 2022 (UTC)

Discussion regarding revision of naming convention for organic compounds

Discussion is occurring at WikiProject Chemicals. Mdewman6 (talk) 00:45, 15 March 2022 (UTC)

Help adding new article to project

Dear All,

I would be most grateful if someone could add this https://wiki.riteme.site/wiki/Glass_formation to the chemistry project. I tried googling to find out how to do so but was unable to find how and don't want to mess things up.

Kind regards EvilxFish (talk) 09:23, 23 March 2022 (UTC)

Done: you add {{Chemistry|class=start|importance=low}} in the talk page. The page would benefit from further editing and certainly needs more references. --Project Osprey (talk) 09:46, 23 March 2022 (UTC)

Thank you, much appreciated and yep it is very much based on that textbook, I did find a review article as well and will see if I can pull anything from that! EvilxFish (talk) 11:45, 23 March 2022 (UTC)

Does FFC Cambridge process warrant its own article?

Hi, I am referring to this https://wiki.riteme.site/wiki/FFC_Cambridge_process which I came across via a link from the titanium article, reading it and checking the one secondary source that mentions it (the review article) I believe it should be something that should be covered on a more general article about titanium production or even as part of the main titanium article. I would love to hear your thoughts, to me personally it just seems like yet another academic self promoting. EvilxFish (talk) 15:36, 23 March 2022 (UTC)

My recollection is that the article did spring out of some self-promotion. If this process continues to prove uncompetitive, then the article will be ignored and is sort of harmless. There are several articles on, for example, drug candidates that didnt not advance. Those quasi-orphaned articles are just ignored.

In my opinion, we should just keep an eye on this Cambridge process to prevent the self-promoters from over promising. More importantly, the related more general articles should not be contaminated by hype or misleading claims. --Smokefoot (talk) 16:44, 23 March 2022 (UTC)

@Smokefoot: Thank you, I've been attempting to asses it's notability as a topic on wikipedia (and going through removing the attempts to promote it even if not relevant on other articles). I looked up the plum metrics for the original paper but beyond that I am a little stuck when it comes to assessing the quality of the citations which is important as per this. I would note apart from possibly meeting "Widely cited", it has definitely failed every other possible noteworthy category. If you agree it does not meet that criteria I will create the deletion discussion, but am currently unsure. EvilxFish (talk) 17:11, 25 March 2022 (UTC)

What is Parent Structure?

The definition of "Parent Structure" is the most meaningless, least helpful definition I have ever read. If you are an experienced chemist, perhaps you can in your mind extract from those words something that you think the author meant to say. But if you had only two semesters of chemistry in college, like me, then the definition is absolute gibberish. The image is captioned "Inorganic parent structure" but there is no explanation whatsoever.

Mulehide (talk) 05:51, 26 March 2022 (UTC)

"The definition of "Parent Structure" is the most meaningless, least helpful definition I have ever read." Really? Ever? --Smokefoot (talk) 13:44, 26 March 2022 (UTC)

Thanks for adding a proper intro to the article, Smokefoot! I hacked some more on it. DMacks (talk) 18:33, 26 March 2022 (UTC)

Eyring Equation and Enthalpy of Activation

Dear WikiProject Chemistry,

I would like to kindly request that an article be written on Enthalpy of Activation in the Eyring Equation. I don't have experience in Chemistry so I didn't know which section of the article requests on Wikiproject Chemistry to place this under. I would also request that the symbol used for enthalpy of activation in the Eyring Equation article is changed from ΔH‡ to Δ‡H⚬. The first symbol is incorrect according to IUPAC: https://goldbook.iupac.org/terms/view/E02142. I am requesting an article on this because I am referencing a page called the List of Mathematical Uses of Latin Letters and enthalpy of activation came up. I do not have an appropriate article to link this chemical kinetics term to. I hope one of your fine chemists could help me out! If you have any questions please come to my talkpage! Kabiryani (talk) 11:57, 2 April 2022 (UTC)