Wikipedia talk:WikiProject Chemistry/Archive 59
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Request for review: Draft:American Peptide Society 2
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I am seeking input from WikiProject Chemistry members on Draft:American Peptide Society 2, an article about the American Peptide Society — a nonprofit scientific organization founded in 1990 that hosts the biennial American Peptide Symposium (dating to 1968) and publishes the journal Peptide Science through Wiley. === Background === The article has been declined twice at AfC, with reviewers stating that "all sources are primary." However, the article includes independent secondary sources from: * ProPublica Nonprofit Explorer * FASEB (listing APS as a member society) * University of North Carolina and University of Bristol chemistry departments (award announcements) * Chemical & Engineering News * Wiley Online Library === Why I'm asking here === The American Peptide Society is comparable to organizations like the Protein Society and Biophysical Society, both of which have Wikipedia articles with fewer independent sources. I believe the article meets notability guidelines for scientific organizations and would appreciate a review from editors familiar with chemistry-related content. The article covers: * History and founding (1990) * The American Peptide Symposium series (29 meetings since 1968) * Awards (Merrifield Award, du Vigneaud Award, Hirschmann Award, etc.) * Publications (Peptide Science journal, proceedings volumes) * Notable members and international collaborations === Disclosure === I have disclosed my connection to APS via {{connected contributor}}. Any feedback on improving the article or navigating the AfC process would be greatly appreciated. Larssahl (talk) 17:22, 26 January 2026 (UTC) | |
- @Larssahl: It is clear that you are using an LLM in the draft in this reply. According to the decliners, the draft has a promotional tone, and you have not provided any secondary sources about this organization. Write a rap about how we can address the issues with your draft, and why you are seeking our help. –LaundryPizza03 (dc̄) 18:44, 26 January 2026 (UTC)
- Hi @LaundryPizza03, thanks for engaging. You're right in that I have used an AI tool to help process sources and format citations. I am not a Wikipedia expert and was trying to get things right. However, I am very much a real person who has been associated with the American Peptide Society since 2011, when, as a Communications Staff member of the Chemistry Department at UNC Chapel Hill, I began doing graphic design for the 2013 Symposium in Kona, Hawai’i, which coincidentally was held there since I lived in Kona for almost 20 years and recommended the location to the two co-chairs of that year, Professors Marcey Waters and David Lawrence, both at UNC CH. Since then, I have built and created websites and content both for the Society itself and its biennial symposia. In that capacity, I have also taken about 12,000 photographs and a large library of videos for the Society.
- This effort is part of an almost pro bono effort by me. I am paid only a nominal fee for the web work I do. The Wikipedia page is something I volunteered to do as a compliment to my other outreach, and is both a personal challenge and a work of aloha for the people of the APS. During my years at UNC, I fell in love with this work and after my recent retirement, it has become a treasured connection to both the science and the people. Parenthetically, I hold a Master's Degree in Technical Communication.
- On the substance: the second decliner stated "all sources are primary," but that is not accurate. After the first decline, I added several independent secondary sources:
- · ProPublica Nonprofit Explorer - verifies 501(c)(3) status
- · FASEB.org - confirms APS membership in this federation of 130,000+ researchers
- · University of North Carolina and University of Bristol press releases - independent coverage of APS awards
- · Chemical & Engineering News - coverage of Ralph Hirschmann
- · Wiley - publisher of the Society's journal
- I am asking for your kind help as I see comparable society articles such as Protein Society, and the Biophysical Society, exist with fewer sources, and to the best of my ability I addressed the "primary sources" concern, but the reviewers have not engaged with that point.
- As for the rap, I respectfully decline, but appreciate the humor. Happy to become part of a discussion that improves this work and allows the article to be published.
- Aloha - Lars Larssahl (talk) 21:45, 26 January 2026 (UTC)
- One of the main things needed is secondary about the organization itself. Not simple directory-info, public filings, etc. DMacks (talk) 21:51, 26 January 2026 (UTC)
- Thank you, @DMacks — that's a helpful clarification. I understand the distinction now: verification of facts vs. substantive coverage of the organization itself. I will search for existing secondary coverage and may pursue media outreach to generate such coverage. I appreciate the guidance. –~~~~ Larssahl (talk) 14:12, 27 January 2026 (UTC)
- Please don't try and generate your own coverage. To begin with, look at the notability criteria for determining whether Wikipedia should have an article on a given organization. Our term "notability" can be a bit misleading, as it's obvious to anyone who does a bit of digging that the APS is a big deal. Rather, we use it as shorthand for the existence of in-depth coverage, independent of the original organization, in multiple secondary sources (e.g. books or review articles), allowing a substantial article to be written based on these sources. In other words, you'll need to find 1–2 more references like this:
- Merrifield, Bruce (1993). Life During a Golden Age of Peptide Chemistry. Washington, DC: American Chemical Society. ISBN 978-0-8412-1842-0.
- Here are some other references I found that are not substantive enough to strongly support notability, but may be of use when writing the article:
- Shimonishi, Yasutsugu (2002) [1997]. "Preface". In Shimonishi, Yasutsugu (ed.). Peptide Science — Present and Future | Proceedings of the 1st International Peptide Symposium. Dordrecht: Springer Science & Business Media. pp. xxxv–xxxvi. ISBN 978-0-306-46864-3.
- "Josef Rudinger Memorial Award 2018". The European Peptide Society. 2018-05-06. Retrieved 2026-01-27.
The Merrifield ... [Award], administered by the APS, ... recognize[s] the highest achievements in the chemistry ... of peptides at an international level
- "2022 Nobel Prize in Chemistry awarded to Morten Meldal". The European Peptide Society. 2022-10-08. Retrieved 2026-01-27.
some of the most prestigious awards in peptide science, including the Vincent du Vigneaud Award by the American Peptide Society
- After you've found enough good references, rewrite the article to be primarily based on them. Some citations of first-party sources will be inevitable, but try not to include too many, even if it means shortening the article substantially. After you get that through AfC, you can use WP:Edit requests to request expansions as necessary. Though also bear in mind that WP articles should follow summary style, rather than covering every last detail of a particular topic. Preimage (talk) 15:57, 27 January 2026 (UTC)
- Please don't try and generate your own coverage. To begin with, look at the notability criteria for determining whether Wikipedia should have an article on a given organization. Our term "notability" can be a bit misleading, as it's obvious to anyone who does a bit of digging that the APS is a big deal. Rather, we use it as shorthand for the existence of in-depth coverage, independent of the original organization, in multiple secondary sources (e.g. books or review articles), allowing a substantial article to be written based on these sources. In other words, you'll need to find 1–2 more references like this:
- Thank you, @DMacks — that's a helpful clarification. I understand the distinction now: verification of facts vs. substantive coverage of the organization itself. I will search for existing secondary coverage and may pursue media outreach to generate such coverage. I appreciate the guidance. –~~~~ Larssahl (talk) 14:12, 27 January 2026 (UTC)
- Instead of using LLMs for reference processing, I would suggest User:Citation Bot. Fishsicles (talk) 14:26, 27 January 2026 (UTC)
- One of the main things needed is secondary about the organization itself. Not simple directory-info, public filings, etc. DMacks (talk) 21:51, 26 January 2026 (UTC)
Mass AfD nominations of chemistry related data pages
Please note that User:An anonymous username, not my real name and perhaps some others have very recently done mass AfD nominations of Chemistry related data pages. So far I have seen ones for Boiling points of the elements (data page), Lithium chloride (data page), Melting points of the elements (data page) and Atomic radii of the elements (data page); there may be more science related pages done or planned. Maybe I missed it, but this is certainly something that I think should have been discussed here first for a concensus.
You can express opinions on this both here and at the respective AfD pages (go to the main page then follow the link). AfD discussions are typically open for at least 7 days. Ldm1954 (talk) 02:12, 3 February 2026 (UTC)
- Comment, there have been multiple comments/votes at the AfD pages, which to me tend towards WP:SNOW keep. There are a few issues on data pages for specific compounds as mentioned below by Fishsicles which I think merit further discussion to establish a consensus for the future. Ldm1954 (talk) 16:24, 3 February 2026 (UTC)
- In my view, at least some of (the information in) these data pages should be moved to WP:Workpages, to be stored in the project workspace rather than the article namespace. E.g. the comparison of values between different sources in Melting points of the elements (data page) is relatively unusual for an article (we'd normally either list the most reliable value or provide a range, rather than 3+ different values), but necessary for our work behind the scenes to
maintain consistency across content
. - NB. If we do decide to turn some data pages into workpages, links to them will need to be moved from articles into the banner of related talk pages so that editors can continue to easily find them. See WP:Source assessment for a separate but related use case for workpages. WP:MAINSPACE categorizes data pages as
Pages in mainspace that are not universally considered articles-proper
, similar to lists, disambiguation pages, and set index articles. The old posts from User:Bluerasberry at Category talk:Chemical data pages#Nature of these data pages and from User:Piotrus at Wikipedia talk:Workpages#Workpages are dangerous and should be avoided may also be of relevance to this discussion. Preimage (talk) 17:07, 3 February 2026 (UTC)- (Update: After thinking it over, I think NLIST applies. I've !voted accordingly at the deletion nominations.) Preimage (talk) 05:50, 4 February 2026 (UTC)
- I am for deletion in this case. The datapage information should be stored in Wikidata and imported to the infoboxes as needed on Wikipedia. The information provided is relevant and should be included on Wikipedia somewhere, but a whole separate page that is not easily accessible to the reader and features poor formatting is not it. Jg.lamp (talk) 21:25, 3 February 2026 (UTC)
- Need a plan to move to Wikidata These pages are from 2005 and by Wikipedia and comparable Internet publishing standards, this content was acceptable then. We have had Wikidata since 2012 and Wikidata could accept content like this since about 2017 or so. I get that we need a transitional period to migrate data and that have limited labor, partnership, and staff resources to do this. It is tolerable to keep this content in Wikipedia for longer but every year that passes without a plan to move this to Wikidata and interconnect this with Wikipedia is problematic. We have no in-line citations. There are a thousand data points to verify, and we are relying on trust in anonymous editors when increasingly we need more systematic verification. Wikipedia is not at all a place to have human editors manage verification of tables of numbers. Wikidata can do these things, but actually we cannot well manage it there, and even if we could there is no way to move a Wikidata verified table of numbers into Wikipedia.
- I think a table like this is in-scope for Wikipedia. There are some tables we need in Wikipedia for general reference, for certain fields. I am comfortable keeping these for years longer but we do need a plan to migrate this kind of content to structured data management systems. Bluerasberry (talk) 15:32, 4 February 2026 (UTC)
Cleanup needed: Onium ion
A lot of the ions listed on this page seem to be extrapolations of periodic trends, not anything actually established to exist - and I very much doubt these periodic trends apply unconditionally (e.g. the assumption of astatine and tennessine acting like the other halogens is AFAIK still rather spurious). The page also doesn't distinguish between onium ions with stable parent hydrides and those only prepared as organyl derivatives. My opinion is that everything here should be removed unless reliable sources attest to the ion's actual existence; ideally we should further distinguish ions by whether they're only known in the gas phase, known in solution (whether an adduct or not), or known in actual compounds, but to me this is less significant than pruning out things that are unlikely to even exist. Fishsicles (talk) 15:28, 4 February 2026 (UTC)
- I am supplying references, and neutralising likely original research/guess work. Some of those terms only appear in Wikipedia and not previously published. Graeme Bartlett (talk) 13:22, 5 February 2026 (UTC)
Entropy and enthalpy values for non-STP states in Chembox
Going through the data page cleanup discussed previously, the main value that has not found a direct correlate is entropy and enthalpy values for non-STP states. Before clogging up the Template:Chembox talk page with requests for additions of deltaH of fusion/vaporization/formation for each state, I wanted to ask here what would be best. Jg.lamp (talk) 21:55, 6 February 2026 (UTC)
Chemistry data page cleanup
Going off the prior discussion, I've been looking at some of the single-compound pages like calcium hydroxide (data page). These pages seem mostly superfluous with the contents of a chembox, and some of them (as the aforementioned) have a bunch of empty entries. Is there a reason for maintaining these as separate pages rather than integrating them into compound pages as part of the chembox or perhaps collapsible tables? Fishsicles (talk) 16:11, 3 February 2026 (UTC)
- Some pages, such as Water (data page) include extensive data on spectroscopy and thermodynamics that would be impractical to include in Chembox in sheer size. Collapsible tables is an idea. Might be an idea to keep data pages that are this extensive and merge/remove data pages that include very little data such as CaOH. Jg.lamp (talk) 21:27, 3 February 2026 (UTC)
- There have been several previous projectspace discussions about these pages: AfDs, Village Pump discussions, WT:CHEM, WT:CHEMS. For reference I've appended a table of previous AfDs (i.e. excepting the four open right now); I haven't yet read the other discussions listed here. Preimage (talk) 07:20, 4 February 2026 (UTC)
Chemistry data pages: previous AfDs
| AfD | Opened | Result | Comments |
|---|---|---|---|
| Wikipedia:Articles for deletion/2-Pyridone (data page) | 2024-06-01 | Merge | Unanimous merge to 2-Pyridone#Analytical data. Comments include I wondered if all of these Category:Chemical data pages would need consistent outcomes. I found a few discussions, such as Wikipedia talk:WikiProject Chemistry/Archive 36 § Data pages and Wikipedia talk:WikiProject Chemistry/Archive 50 § Chemical data pages - move to Wikidata?, and the consensus seems to be that they're decided on a case-by-case basis. |
| Wikipedia:Articles for deletion/Elastic properties of the elements (data page) | 2022-12-25 | Keep | Excepting the nom, unanimous consensus to keep |
| Wikipedia:Articles for deletion/Caffeine (data page) | 2022-01-15 | No consensus | The DPCLEANUP closure request notes active discussion moved to this AfD, which concluded with a recommendation to initiate a broader discussionon chemical data pages (say, at WP:VPP). |
| Wikipedia:Articles for deletion/Phenyldichloroarsine (data page) | 2021-12-31 | Speedy delete | Page without any useful information, just placeholders. Comments include Article is part of a 140P set "(data page)" merge/delete/keep discussion is ongoing at Wikipedia talk:WikiProject Chemicals § Chemical data pages cleanup (WP:DPCLEANUP). Straight deletion is disputed. The issue is foremost WP:CHEMICALS content & chemical data, so not suited for XfD this way yet. I propose an early close, and allow the discussion to bear fruit first. For sure, this actual XfD should not interfere with or prejudge that discussion. |
| Wikipedia:Articles for deletion/Toluene diisocyanate (data page) | Page did not contain any useful information | ||
| Wikipedia:Articles for deletion/Aluminium sulfate (data page) | 2021-12-31 | Speedy keep | Withdrawn by nom with edit summary close and wait for ongoing discussion |
| Wikipedia:Articles for deletion/Antimony trioxide (data page) | |||
| Wikipedia:Articles for deletion/Phosphorus tribromide (data page) | |||
| Wikipedia:Articles for deletion/Beryllium oxide (data page) | |||
| Wikipedia:Articles for deletion/Tetramethylethylenediamine (data page) | |||
| Wikipedia:Articles for deletion/Hydrochloric acid (data page) | |||
| Wikipedia:Articles for deletion/Tin(II) chloride (data page) | |||
| Wikipedia:Articles for deletion/Potassium nitrate (data page) | 2021-12-31 | Speedy keep | Withdrawn by nom with edit summary close and wait for ongoing discussion. Comments before withdrawal include it looks like there's a new consensus building on WT:Wikiproject chemicals about data pages, It seems like there may be consensus building to merge these pages to wikidata, and Rightly or wrongly, the consensus is that common chemical compounds have data pages on Wikipedia. |
| Wikipedia:Articles for deletion/Chloric acid (data page) | 2021-12-31 | Speedy keep | Withdrawn by nom with edit summary close and wait for ongoing discussion. Subsequently deleted on 2022-01-04 under WP:CSD#A3. |
| Wikipedia:Articles for deletion/Arsenic trioxide (data page) | Withdrawn by nom with edit summary close and wait for ongoing discussion. Subsequently deleted on 2022-01-05 with edit summary A3: Article that has no meaningful, substantive content: only consists of placeholders except of an external link that was copied to Arsenic trioxide, per discussion at Wikipedia talk:WikiProject Chemicals. | ||
| Wikipedia:Articles for deletion/Diborane (data page) | 2021-12-22 | Delete | Page did not contain any information not already contained in the chembox of Diborane. Almost unanimous consensus to delete. |
| Wikipedia:Articles for deletion/Acetonitrile (data page) | 2015-10-15 | Withdrawn | Withdrawn by nominator within 1 minute; closed 2022-07-23 with the note This AfD was never properly opened, so it was never properly closed. |
| Wikipedia:Articles for deletion/Water (data page) | 2015-08-27 | Keep | Excepting the nom, unanimous consensus to keep. Nom mentions their previous proposal (to move chemical data pages to talk page subpages) at WT:WikiProject Chemicals/Archive 2012#Chemical data pages (albeit this did not get much discussion at the time) |
| Wikipedia:Articles for deletion/Sulfuric acid (data page) | 2014-08-31 | Speedy delete | Contested PROD, closed as speedy delete within 3 hours of nom and with no other AfD comments. Justification provided by the admin closer was Didn't realise redirect caused technical problems, no reason to keep this a week since no one want to actually keep |
| Wikipedia:Articles for deletion/Yttrium(III) oxide (data page) | 2007-03-10 | Keep | Discussion split evenly between keep and merge, closed as keep with justification No one besides the original nominator argues for deleting the content outright. Merging the data is an editorial decision that anyone can perform if they feel like it. Merge to Yttrium(III) oxide implemented 2007-04-03 (added one sentence on thermal conductivity, accidentally? moved into the lede 2018-01-03, where it remains to this day). |
| Wikipedia:Articles for deletion/Bentiromide (data page) | 2007-01-09 | Merge | Contested discussion, closed as keep and merge into appropriate page(s). Merge to Bentiromide (OrganicBox template) implemented 2007-01-18. |
Current status and near-term proposal
Category:Chemical data pages, which are the data-pages about individual compounds, currently has 132 articles. That's not nearly as large a number as I had thought, so the scale of the work needed if we decide to make major changes is not as bad as I feared. Further, as others have noted, there are often many skeleton tables with few or no data values. I propose as an initial cleanup two actions:
- Merge data that have analogous ChemBox fields into the chemical's actual article (and catching contradictory info). Given we have at least implicit consensus that those data-types are appropriate for ChemBox, let's make sure we provide that info there when it's available. That way there's a standard first-choice place for readers to find those types of data. The data-pages do not even all have a standard format, so it's needlessly hard to machine-parse, unlike the standardized ChemBox/DrugBox.
- Send to AFD individual data-pages that have no data beyond what's in the article's ChemBox. That reduces WP:CFORK-like duplication, making it easier to keep what we have up-to-date and vandal-free. It also helps others who want to use our data find it more readily by keeping data-pages as solely more-detailed supplements when we actually have something more to say than the ChemBox. This step towards unification also helps anyone who wants to work on migrating the data to wikidata.
Once we are down to only having data-pages for cases where they actually have unique information, we can decide what to do with that information. DMacks (talk) 15:57, 4 February 2026 (UTC)
- Seconding this for the immediate term. I suspect that the more complete pages, as the aforementioned water (data page), will need to be handled on a case-by-case basis anyway.
- There is an extant Category:Chemical data pages cleanup that appears to have been populated by a prior discussion and may be of use. I suspect a maintenance category for filtering out those data pages with data in excess of chembox would also be valuable. Fishsicles (talk) 16:04, 4 February 2026 (UTC)
- I'm starting out by pruning empty or redundant entries from pages. This should also give us a list of parameters that would need to be added to chembox. Relative density is currently on the list from my clearing out arsine (data page). Fishsicles (talk) 16:19, 4 February 2026 (UTC)
- And that helps uncover ENGVAR of the number formats, which would create a massive mess if it were machine processed based on an assumed canonical form. DMacks (talk) 16:50, 4 February 2026 (UTC)
- Looking at caffeine (data page) versus caffeine, it may be worth a modification to {{Infobox drug}} to support subtemplates such as {{Chembox Identifiers}} to unify how chemical properties are displayed across chemical articles in general and drug articles. And also to make the merge easier, I won't pretend otherwise. (I'm not as much up on pharmaceuticals - too many moving parts once you get into biology - are there sensible reasons to have the drug infobox not be an expansion of chembox with additional sections, rather than a wholly separate template?) Fishsicles (talk) 17:28, 4 February 2026 (UTC)
- That's a reasonable discussion, but I think for another day. You wouldn't be the first to ponder it (it's been discussed before, but not in a long time IIRC). Perfect is the enemy of good has doomed many WP-wide overhauls in the past. DMacks (talk) 13:34, 5 February 2026 (UTC)
- The template namespace, long standardised, must specialise; long specialised, must standardise. Thus has it ever been.
- All jokes aside, I agree it's probably an idea best examined in of itself. Fishsicles (talk) 14:10, 5 February 2026 (UTC)
- That's a reasonable discussion, but I think for another day. You wouldn't be the first to ponder it (it's been discussed before, but not in a long time IIRC). Perfect is the enemy of good has doomed many WP-wide overhauls in the past. DMacks (talk) 13:34, 5 February 2026 (UTC)
- I'm starting out by pruning empty or redundant entries from pages. This should also give us a list of parameters that would need to be added to chembox. Relative density is currently on the list from my clearing out arsine (data page). Fishsicles (talk) 16:19, 4 February 2026 (UTC)
- So with the pages that are clearly able to be merged into Chembox on their main page, such as calcium hydroxide (data page) or difluoromethane (data page) and has been done so, are they good to list on AfD? Of note, the LiCl datapage is strongly leaning keep on its current AfD discussion. Jg.lamp (talk) 15:36, 5 February 2026 (UTC)
- I would prefer to perform the prune and merge and then list the page for deletion, just so any lingering questions can be looked at - there's no real rush for these stub pages. For example, my one question with calcium hydroxide (data page) is that some of the data is slightly different from the chembox (specifically enthalpy of formation). How should we choose which value to keep? It's almost certainly a matter of experimental error - I suppose it's noted as ΔfH⦵solid rather than ΔfH⦵298 so it could be a different temperature, though I think it's very doubtful a reference text would depart from that convention.
- Should we keep the value with more significant figures, which may be measured on more precise instruments - or may indicate nothing, and simply be published with different numeric style guidelines? Should we keep values from the newer source? Should we maintain the table of potential sources for migration to Wikidata?
- Those aren't rhetorical questions. We should probably standardise how we handle these things, or at least have a heuristic. Fishsicles (talk) 16:36, 5 February 2026 (UTC)
- Funny enough, we both did the CaOH edit within a couple minutes of each other but it is only showing one of the values!
- I think the best is use the newer value assuming it has a lower standard of error/higher accuracy. For migration to Wikidata, it might be better to use values from one of the big databases, like PubChem, by default.
- Some of the datapoints in the database aren't in the Chembox either - difluoromethane has a bunch related to its thermodynamics as a refrigerant that seem extremely relevant. When I get time later today, I am going to propose some new variables for the template subsections to include these and go from there. Jg.lamp (talk) 16:45, 5 February 2026 (UTC)
- How about changing it from to either or so we can keep track of those someone has checked and triaged as ready for AFD vs needing further discussion. DMacks (talk) 18:50, 5 February 2026 (UTC)
- Sounds like a good idea, though I would suggest a division of "unmergeable" into Category:Chemical data pages (Chembox parameter needed) and Category:Chemical data pages (large tables) to separate pages that could be merged if additional parameters were added to chembox from those that have large tables of data that would be difficult to fit in a chembox (e.g. large amounts of solubility by temperature/spectroscopic data). Fishsicles (talk) 18:58, 5 February 2026 (UTC)
- Sure. The (merged), (Chembox parameter needed) and (large tables) category links are now blue, and are subcats of Category:Chemical data pages so we can find them easily. DMacks (talk) 19:09, 5 February 2026 (UTC)
- Sounds like a good idea, though I would suggest a division of "unmergeable" into Category:Chemical data pages (Chembox parameter needed) and Category:Chemical data pages (large tables) to separate pages that could be merged if additional parameters were added to chembox from those that have large tables of data that would be difficult to fit in a chembox (e.g. large amounts of solubility by temperature/spectroscopic data). Fishsicles (talk) 18:58, 5 February 2026 (UTC)
- Priority: Several infoboxes list separate standard entropy/standard enthalpy of formation/etc. for various phases of a compound, using e.g. ΔfH⦵gas. Now, obviously aluminium chloride is not a gas at standard temperature and pressure; NIST (the source for these values) performs additional calculations to find these values based on chemical equilibria. This data is worth having, and for the moment I've been merging them into the main standard enthalpy chembox with phase indicators, but sooner rather than later we might want to update {{Chembox Thermochemistry}} to separate these values from "true" standard enthalpy. Fishsicles (talk) 20:10, 5 February 2026 (UTC)
- I see some H-bond donor/acceptor counts in the data pages, which I think we can ignore even though there are no chembox fields for them. They are widely available in PubChem and ChemSpider database and are machine-generated/generatable from the structures themselves, which are sufficiently defined in SMILES, etc. Interestingly, those two databases do not always agree with each other. If wikidata wants them, they can choose their database source and cite it, or choose their algorithm and identify it. If reliable sources disagree, we should either include them all or none, and the (data page) pages do not always cite their source. DMacks (talk) 23:56, 7 February 2026 (UTC)
I was quite surprised about this move, since "hydroxy" seems appropriate (see e.g. doi:10.1351/goldbook.A00204). Furthermore, articles in Category:Functional groups do not tend to have "functional" in their name. Leyo 20:32, 16 February 2026 (UTC)
- I recommend undoing that move. There are sufficient implications that such a move would require discussion.--Smokefoot (talk) 21:25, 16 February 2026 (UTC)
- That's certainly not a clear-cut uncontroversial move (and for the record I oppose it)...definitely should be undone promptly. DMacks (talk) 21:29, 16 February 2026 (UTC)
- I have reverted the moved. @VidanaliK: you may wish to join this discussion to explain your reasons for a move. Graeme Bartlett (talk) 11:02, 17 February 2026 (UTC)
- Stated reason for the move was
- the actual name of the group is hydroxyl; hydroxy- is just the prefix
- I'm very curious about a source on this, as it's contrary to every prescriptive distinction that I've seen, which favours "hydroxyl is the radical, hydroxy is the group" (as the linked Gold Book definition above). Usage of "hydroxyl" beyond simply the radical is still in sufficiently common use for me to consider it as a synonym (even IUPAC does it sometimes), but to assert hydroxy is "just the prefix" without citation while moving a major page is... spurious. Fishsicles (talk) 16:14, 17 February 2026 (UTC)
Chembox request
I am making this request as a researcher, rather than a Wikipedian. I would like to see, when possible the following in the data for chemicals: band gap, electron affinity, ionization energy (first). The HUMO/LOMO pair could be substituted for EA and IE although they are not the same. This could either be in the box or the data page. Ldm1954 (talk) 20:33, 21 February 2026 (UTC)
- Band gap is already in Template:Chembox Properties. Is this edit the sort of thing you were thinking of?
- Electron affinity and ionization energy would need to be added. Unfortunately our regular chembox maintainer was banned a couple of years ago, though I suspect there are some other regulars around that might be able to do that for you.
- The paper Bredas, Jean-Luc (2014). "Mind the gap!". Materials Horizons. 1 (1): 17–19. doi:10.1039/C3MH00098B. (cited by HOMO and LUMO) claims
The calculated HOMO–LUMO gap, i.e., the difference between the calculated HOMO and LUMO energy levels, only provides an approximation to the fundamental gap; the quality of that approximation strongly depends on the specifics of the computational methodology
. I think that indicates that the HOMO–LUMO gap, which isn't directly measurable, isn't guaranteed to be consistent between different sets of quantum-chemical calculations either, which suggests it might be best to avoid (though I'm sure you know a lot more about this than I've been able to learn). Preimage (talk) 13:37, 22 February 2026 (UTC)- That type of edit is what I was thinking of.
- EA & IA can be measured and are more reliable than calculated HOMO/LUMO as you say, but often have not been measured. Ldm1954 (talk) 14:28, 22 February 2026 (UTC)
- You could try asking at Template_talk:Chembox. The template is protected from regular editors. Johnjbarton (talk) 17:46, 22 February 2026 (UTC)
It would be sweet if someone could add additional sources. Bearian (talk) 00:37, 20 February 2026 (UTC)
- @Bearian I see that Google Scholar has over 300 just looking within article titles, so expanding WP should be easy. I'm otherwise engaged at present. Mike Turnbull (talk) 11:47, 23 February 2026 (UTC)
- Thank you for the link! Bearian (talk) 13:05, 23 February 2026 (UTC)
Done - great work by Graeme Bartlett and Smokefoot! Bearian (talk) 13:08, 23 February 2026 (UTC)
- Thank you for the link! Bearian (talk) 13:05, 23 February 2026 (UTC)
Move Grignard reagents to "halide"?
We have a number of pages on Grignard reagents: CH3MgCl, C2H5MgBr, C3H7MgBr, (CH3)2HCMgCl, C3H5MgBr, C6H5MgBr. The pages seem to vary between the bromide and the chloride, but typically other RMgX compounds are present as redirects - e.g. methylmagnesium iodide and methylmagnesium bromide both point to methylmagnesium chloride (even though that page itself claims that the bromide is the more common form of CH3MgX).
This vexes me. I doubt that each individual halide warrants a page for its slight differences from the analogues, but neither should a chloride redirect to a bromide as if they are synonyms. My thought would be to move these pages to either e.g. methyl Grignard reagent or methylmagnesium halide. I can't say I like either of these solutions but I think I like them more than status quo. Any other thoughts? Fishsicles (talk) 18:43, 23 February 2026 (UTC)
- This messiness doesnt bother me, but I confess to liking the slightly chaotic and eclectic style here, which says to me: "we've got you covered". I once had triethyloxonium redirect to trimethyloxonium because the information would be nearly equivalent and useful, but that approach got firmly slapped because they are different species. In my view, that change placed priority on "order" over helpfulness.
- But I respect your tastes if you want to lobby to unify all the methyl and all the phenyl Grignards. I think that chloride/bromide-based Grignards are more significant commercially because of cost factors, but academic contributors like bromide/iodide end of the halide spectrum.
- Another complication in the Grignard business is that they dont exist without ether coligands: some have Et2O and some thf.
- For people who are really into these reagents, the halides may make a difference, i.e. cross coupling with MeMgCl might differ from MeMgBr (BTW, I need to check but I think that we might gloss over the presence of LiX in some organolithium reagent pages).--Smokefoot (talk) 21:00, 23 February 2026 (UTC)
- Yeah, the key question I have - and one that I'm not nearly informed enough about the internal mechanisms of the Grignard to answer - is whether the halide has any particular effects. In my experience the literature usually defaults to bromide; the explanation as I've been told is that it's easier to prepare the Grignard with a heavier halogen because the CX bond is weaker. What I'd want a more detailed analysis on - which may not even exist, as AFAIK the Grignard's internals are still a bit fuzzy - is how that in turn effects the performance of the actual Grignard reaction.
- I understand on one hand wanting to keep things casual. as any distinctions between these reagents in practice is beyond my ken, but I'm also leery of equating too many chemical species in the age of machines that lie to you. doi:10.7326/aimcc.2024.1260 shows the risk of those equivalences getting bandied about where they don't belong. Fishsicles (talk) 01:33, 24 February 2026 (UTC)
- The halide sometimes does have a relevant difference. One notable is the solubility of the RMgX, if you are trying to run a reaction fairly concentrated. Another is the ease of the metallation (I designed an undergrad experiment that easily quantifies the significant rate dependence on X, though the students had forgotten too much gen-chem to discuss it in terms of redox potentials). More-practical concerns are the financial, safety, and stability concerns of the RX precursor, leading to some X being more popular than others. DMacks (talk) 02:22, 24 February 2026 (UTC)
- Redirects are designed to help the reader find information on a topic when there isn't a page named for the specific topic but the topic is covered in some other page. It's not only for alternatives of the article topic itself (synonyms, etc.), but "Subtopics or other topics that are described or listed within a wider article. (Such redirects are often targeted to a particular section of the article.)". If, for example, article A is about notable topic A but also covers topic B that doesn't have its own article for whatever reason, a redirect B→A is exactly within guideline.
- If a certain RMgX reagent (a specific R and X) is notable enough to have an article, then WP:GNG and WP:NCHEM both say it's reasonable to hvae an article about it with its name. If several variants (other X) are not notable enough on their own except as variants, it's reasonable to make them a subsection (possible header "Other halides"). That's analogous to how we often cover modifications of reaction protocols that have different names in the main article about a major named reaction rather than having a generic-named article about the reaction type. Given our desire to have chemboxes, I think it's cleaner to have separate articles for each specific X than to have just an article on the class, to make sure that the chembox actually fits the guidelines for infoboxes ("for the article, at the top, containing key info"). DMacks (talk) 02:15, 24 February 2026 (UTC)
- Status quo. After reading these comments, I'd say leave alone the articles on the individual RMgX's. Gosh knows, for the transition metal (as well as organic) halides, we have individual articles for each halide variant.--Smokefoot (talk) 03:53, 24 February 2026 (UTC)
- Yeah, this sounds best now that you articulate it. An "other halides" section can introduce the alternatives, and if as it develops there's enough specific information about them, it can easily be spun out to another RMgX page. Fishsicles (talk) 14:03, 24 February 2026 (UTC)
Rhodium#Chemical_properties
Could someone with copy of Cotton or similar look at the third paragraph of Rhodium#Chemical_properties? Only the last sentence is sourced. Johnjbarton (talk) 00:59, 5 March 2026 (UTC)
You are invited to join the discussion at Talk:Pinnick oxidation § Proposed merge of Lindgren oxidation into Pinnick oxidation, which is within the scope of this WikiProject. Staraction (talk · contribs) 07:57, 11 March 2026 (UTC)