Chemicals NA‑class

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An editor has requested for Alpha hydroxy acid to be moved to another page. Since you had some involvement with Alpha hydroxy acid, you might want to participate in the move discussion (if you have not already done so).

Hi all,

It's been a while and I hope everybody's been well. I'm not active anymore, but the recent renaming of the above two articles to terminal alkene and straight-chain terminal alkene caught my eye.

To this chemist, alpha-olefins, linear alpha-olefins, and polyalphaolefins are articles of commerce useful in making polyethylene, detergents, lubricants, and other materials. Terminal alkenes refer to the specific moiety in scientific literature. Not quite the same thing.

Could I please ask this community to review the change? Thanks! --Rifleman 82 (talk) 16:13, 15 October 2023 (UTC)Reply[reply]

The organic books I have (March's 2020 and Clayden 2001) largely ignore *olefin and redirect to *alkene in the index, like the texts that Mdewman6 has. To get a rough sense of usage, Google Scholar gives 1.5 times as many results for "alpha[α][-]olefin[s]" as for "terminal alkene[s]". The ratio decreases to 1.35 when looking only at the past decade, so there's a gradual trend toward terminal alkenes. General Google search gives twice as many alpha-olefins as terminal alkenes, and googling with Bing gives similar results. Maybe industrial usage favors olefins but I'd say there's no clear preference based on WP:COMMONNAME or on overall technical usage. –MadeOfAtoms (talk) 23:21, 15 October 2023 (UTC)Reply[reply]

A literal reading of the both phrases suggests equivalence. I contend that alpha-olefins is a term of art referring to the low MW hydrocarbon, whereas terminal alkenes have a more general meaning that is not restricted to this (very significant) class of industrial products. These low MW materials are largely mature products, so you probably won't see many recent references in Google Scholar. Regardless, I do believe the distinction emerges as you look at the results. As an example, the first 5 hits for each:

Alpha olefin

1. Recent findings and experiences with alpha olefin sulfonates
2. Foam films stabilized with alpha olefin sulfonate (AOS)
3. Performance and anti-wear mechanism of CaCO3 nanoparticles as a green additive in poly-alpha-olefin
4. [BOOK] Tailor-made polymers: via immobilization of alpha-olefin polymerization catalysts
5. [PDF] Model Ziegler-Natta. alpha.-Olefin Polymerization Catalysts Derived from [{(. eta. 5-C5Me4) SiMe2 (. eta. 1-NCMe3)}(PMe3) Sc (. mu. 2-H)] 2 and [{(. eta. 5 …

Terminal alkene

1. Terminal Olefin (1-Alkene) Biosynthesis by a Novel P450 Fatty Acid Decarboxylase from Jeotgalicoccus Species
2. [PDF] Metabolic activation of valproic acid and drug-mediated hepatotoxicity. Role of the terminal olefin, 2-n-propyl-4-pentenoic acid
3. Selective dihydroxylation of non-conjugated dienes in favor of the terminal olefin
4. Selective Isomerization of a Terminal Olefin Catalyzed by a Ruthenium Complex: The Synthesis of Indoles through Ring‐Closing Metathesis
5. High‐Yielding Tandem Hydroformylation/Hydrogenation of a Terminal Olefin to Produce a Linear Alcohol Using a Rh/Ru Dual Catalyst System

--Rifleman 82 (talk) 01:49, 16 October 2023 (UTC)Reply[reply]

Branched chain terminal alkenes are old and often poorly defined. During WWII massive production capacity was developed to provide high-octane fuel for fighter aircraft (see Vladimir Ipatieff). They were often things like 'propylene tetramer', although the name is only loosely accurate. After the war the businesses needed to find a use for these things and they ended up getting used in the developing field of synthetic detergents, amongst others. Branched chains have poor biodegradability and often toxicity issues, so they've been increasingly replaced since the 60s with linear alpha olefins. In my mind the two are closely related. --Project Osprey (talk) 13:52, 16 October 2023 (UTC)Reply[reply]

I recommend that we merge linear alpha olefin into alpha-olefin, which is common jargon. After the merger (the hard part), we consider other names like terminal alkene.--Smokefoot (talk) 14:15, 16 October 2023 (UTC)Reply[reply]

alpha-olefin is currently a redirect. Do you mean to merge linear alpha olefin into terminal alkene? I do agree the two articles should be merged. Mdewman6 (talk) 02:41, 19 October 2023 (UTC)Reply[reply]

Oh, good point (sorry), yes, merge linear alpha olefin into terminal alkene. --Smokefoot (talk) 13:29, 19 October 2023 (UTC)Reply[reply]

From WP:CHEMGROUP: "For groups of compounds named after a simple parent compound, articles about the group should be located at the plural of the parent compound name, e.g. hydrazines, silanes, boranes, diphosphenes." The title "Silane" can be ambiguous because it can either mean the compound Silane or the group of compounds called Silanes, so there has to be two articles with a singular and a plural title. There is also a difference between Phenolate and Phenolates, since "phenolate" refers to the anion, while "phenolates" refers to the group of compounds containing the "phenolate" anion. However in the case of cymene, there is no singular parent compound called "cymene", only three different compounds p-Cymene, o-Cymene, and m-Cymene, so there is no ambiguity with the title Cymene which can only refer to a group of compounds or a mixture of isomers, so I think Cymenes should be moved to Cymene. Same with moving Trimethylbenzenes, Diisopropylbenzenes, and Tetramethylbenzenes to their respective singular titles. In general when there is no possible ambiguity, articles about chemical groups are always singular titled, e.g. Chlorotoluene. Michael7604 (talk) 16:34, 19 October 2023 (UTC)Reply[reply]

Comment: A move request to determine the answer to this concern, as well as possibly establish precedence for this concern, is being discussed at Talk:Diisopropylbenzenes#Requested move 19 October 2023. Steel1943 (talk) 17:22, 19 October 2023 (UTC)Reply[reply]

• Comment. Yes, these pages should have singular titles, because they only discuss isomers of the simple compound, not derivatives of it. They are essentially beefed-up version of chemindices, e.g. Dichlorobenzene, where the isomers are described and linked. Also compare to Cresol, Anisole, etc.. I agree there should be clarification at WP:CHEMGROUP about this distinction; I will amend it once we have consensus here. Mdewman6 (talk) 17:57, 19 October 2023 (UTC)Reply[reply]
• Plural. WP:CHEMGROUP's advice is good. We are chemists, so we know that cymene is not a chemical compound and the article will probably refer to a set of three materials. Most casual readers won't know this and hence they will be assisted by using the plural title. The same principle is used in Wikimedia's categorisation system. It has both "pyridine" and "pyridines": the former for the specific and the latter for the general. (I am aware that this goes against the conclusion at Talk:Diisopropylbenzene#Requested_move_19_October_2023 but that was not a page I had on my watchlist.) Mike Turnbull (talk) 11:14, 1 November 2023 (UTC)Reply[reply]

Is the article copper salicylate about copper(I) salicylate or copper(II) salicylate? The infobox has data mostly for the copper(I) compound, but also for copper(II) salicylate and for a cationic form (PubChem link). The statements about chemical structure in the text (and the cited reference) refer to copper(II) salicylate. The cited reference may be inconsistent as well - I don't have access to the full text of the article, so I'm not sure. Copper(II) salicylate used to be a stub of an article, but has been redirected to salicylic acid. Can someone have a look? Marbletan (talk) 19:17, 31 October 2023 (UTC)Reply[reply]

thank you for catching this problem. The article should probably be about the Cu(II) derivative since copper(II) carboxylates are far more prevalent than the Cu(I) derivatives. It would be a blue solid. Let me do some checking and fix this.--Smokefoot (talk) 21:52, 31 October 2023 (UTC)Reply[reply]

In 2019 Edgar181 changed this from a disalicylate to the mono. In all the early history there was no reference. I added a referenced statement, but that was for a basic copper(II) form. On the chembox front pbchemCID appears to be a copper(I) form despite errors in charge and has 5 hydrogen atoms; CompTox Dashboard (EPA) appears to just copy Wikipedia. ChecmspiderID is also a copper(I). CASNo is for a substance with 6 hydrogens. It references: https://pubs.acs.org/doi/abs/10.1021/ol102407k which is a Cu(II) and has formula with 4 hydrogen atoms and is a brown powder. This brown powder appears to be the same as the dehydrated form seen in https://link.springer.com/article/10.1007/BF02907224 . So hopefully @Smokefoot: you can determine what this article should be about. Does a disalicylate exist? Graeme Bartlett (talk) 23:03, 31 October 2023 (UTC)Reply[reply]

CSD has about 80 structures of adducts. Focusing on the Cu(O₂CC₆H₄OH)₂(H₂O)_x, there are a few examples, Then, focusing on Cu(O₂CC₆H₄O)(H₂O)_x (phenoxide-carboxylate), I could find only one structure. A problem with Cu(II) is speciation in solution, so we dont have those data. In terms of Cu(I), I found one but its got PPh3 stabilizing it. Ullmann's has articles on salicylic acid (and derivs) and "copper compounds", neither article mention copper salicylate, so I conclude that the material is of little or no commercial value. Inorg Synthesis and Brauer's preparative compendium do not mention it. So one preliminary idea might be to make copper salicylate a listing of various hydrates of the Cu(II) material. --Smokefoot (talk) 23:30, 31 October 2023 (UTC)Reply[reply]

My inclination would be to delete this article as it refers to non-notable substance(s). We hardly need articles on all possible salts of a given parent, although some may be warranted, e.g. sodium salicylate. However, I've no objection if someone wants to put in the effort to salvage something. Mike Turnbull (talk) 10:53, 1 November 2023 (UTC)Reply[reply]

I have no problem wiping it out but if you try AFD, you will find that several nonchemical editors ("Elvis editors") suddenly appear and will offer their sage advice and deep concern that something precious is infringed. --Smokefoot (talk) 12:29, 1 November 2023 (UTC)Reply[reply]

I think a WP:TNT is warranted. Blow it up and start over. Graeme Bartlett (talk) 21:30, 1 November 2023 (UTC)Reply[reply]

We could also redirect to copper benzoate, which we could spruce up by listing various derivatives.--Smokefoot (talk) 02:30, 2 November 2023 (UTC)Reply[reply]

I noticed that the chemical structure shown in the article contains a ${\displaystyle \infty }$ symbol and curly brackets. I am not aware of any other polymer article with a similar structure. Unfortunately, MOS:CHEM (incl. subpages) does not provide guidance on how to draw chemical structures of polymers. I would propose removing { }${\displaystyle \infty }$ from the structural formula. Any views on that? Leyo 12:06, 3 November 2023 (UTC)Reply[reply]

Polythene just uses a subscript n, which I think is pretty standard. ${\displaystyle \infty }$ would imply the whole universe was made of nothing but polymethylsiloxane, which wasn't true the last time I looked! Mike Turnbull (talk) 12:26, 3 November 2023 (UTC)Reply[reply]

P.S. The MOS does say Formulae should be readily available, variables like n, x, or y are permissible for substances of variable composition such as polymers. Mike Turnbull (talk) 12:39, 3 November 2023 (UTC)Reply[reply]

What about the following changes:

• Removing { }${\displaystyle \infty }$
• Adding n next to the closing square bracket
• Should it still be · n H2O or rather a different variable (since the number of water molecule does not need to be the same as the number of monomers)?

--Leyo 13:32, 3 November 2023 (UTC)Reply[reply]

You guys are focused on minutia of formating.... The article is unconvincing and reads like a sales pitch, also kinda teachy. This article might be removed, but it does serve a useful purpose in reminding readers that the former USSR was a source of low-level pseudoscientific crap. Some excerpts:

"This product was synthesized in the late 1970s - early 1980s in the USSR by I. B. Slinyakova and I. М. Samodumova of L. B. Pisarzhevskiy Institute of Physical Chemistry[2] (Kyiv), where the theoretical foundations for the formation of the porous structure of organosilicon adsorbents with an adjustable porous structure and a pre-defined chemical nature of the surface were established; "

just nonsense. How would "theory" inform anyone of this ordered double stranded siloxane vs myriad options? Silicates are notorious for crosslinking and complications.

"The study of the use of the preparation was conducted in cooperation with the Medical Service of Krasnoznamennyi Kiev Military District (Medical Service Colonel Professor F. G. Novikov, Medical Service Colonel N. P. Bezlyuda)....The preparation is registered in Russia and the CIS countries ..." More shout outs. --Smokefoot (talk) 12:49, 3 November 2023 (UTC)Reply[reply]

I think Smokefoot is right, considering the significant contributions to the article by an account whose username matches the brand name of the product Enterosgel. Contributions from that user should be removed (or, at the very least, reviewed with a critical eye). Marbletan (talk) 13:18, 3 November 2023 (UTC)Reply[reply]

Yes, there are issues with the article (similar issues are currently also discussed in deWP). I just intended to resolve a (smaller) issue that may be fixed quickly. --Leyo 13:27, 3 November 2023 (UTC)Reply[reply]

The toxicity listing "coho salmon: LC50 = 95 ng/L" should be change to coho salmon: "LC50 = 0.095 micrograms/L" to be consistent with the units of other entries. Also, consider changing the mu symbol for micrograms to mcg as is used in the medical field as it is less likely to be confused with m = milli. Rgbutler (talk) 17:15, 8 November 2023 (UTC)Reply[reply]

All units now in μg/L. We use standard SI symbols. --Project Osprey (talk) 18:21, 8 November 2023 (UTC)Reply[reply]

I'm not sure if the following sentence should really be in the article:

A synthetic route to the 6PPD-quinone has been posted on ChemRxiv.^[1]

I was not able to find the (peer-reviewed) published version of that manuscript. --Leyo 13:26, 17 November 2023 (UTC)Reply[reply]

Agreed ChemRxiv is a preprint server, nothing there passes our usual standard (arXiv itself fails Wikipedia:Reliable sources/Perennial sources). I'm sure there are peer reviewed routes by now.--Project Osprey (talk) 23:06, 23 November 2023 (UTC)Reply[reply]

So far I haven't found any. doi:10.1126/science.abo5785 mentions a commercial standard that has become available. --Leyo 14:44, 24 November 2023 (UTC)Reply[reply]

 You are invited to join the discussion at Wikipedia:Village pump (proposals)#I have came up with new consistency in some articles of chemical compounds. Gain consensus from most other readers and helpful volunteers staying., which is within the scope of this WikiProject. DMacks (talk) 13:18, 29 November 2023 (UTC) DMacks (talk) 13:18, 29 November 2023 (UTC)Reply[reply]

Resolved

Nothing at all. DMacks (talk) 01:12, 30 November 2023 (UTC)Reply[reply]

It doesn't seem immediately relevant to the worklist, but there are a lot of chemicals relevant to lab and industry that do not have articles yet. I asked about this in the teahouse since I didn't know where to go with it and was directed to the red links in List of insecticides, List of herbicides, and List of fungicides as a less overwhelming project than the huge scope of User:Graeme_Bartlett/missing_chemicals and one that is more likely to have a broader range of secondary sources. The list of missing chemicals directed me to Bromopentane from Amyl bromide, which has questionable usefulness compared to just creating articles for the few bromopentanes that exist and makes me wonder how many of these pseudo-disambiguation pages exist for different kinds of substituted alkanes... What approach should I take in cleaning up the missing chemicals, especially the simplersubstituted hydrocarbons? Reconrabbit (talk) 18:55, 29 November 2023 (UTC)Reply[reply]

Indeed, "there are a lot of chemicals relevant to lab and industry that do not have articles yet". There are a also lot of chemicals relevant to lab and industry that do have articles. Where did these articles come from? The predicament is this: the project has grand scope, pretty high standards, but few regular editors. These editors must curate a hefty flux of edits. The same handful of editors then must choose between improving what we have or creating new articles. We are also constrained by "notability" and reliability. So my point is that if you are suggesting that the Chemistry project is imperfect and incomplete, we know but we are proud of what we've produced.

A good way for you to start is to give us some detail of what is needed. Yours imperfectly, --Smokefoot (talk) 23:41, 29 November 2023 (UTC)Reply[reply]

I apologize - I'm very new to all of this and have been (and continue to be) massively impressed with the pages that are here and how far reaching the scope is. I am not a subject matter expert - I tend not to spend too much time in any particular lab in my profession - but I would like to contribute to the project with the tools available. Many of the articles in the worklist have since been improved significantly since they were first listed, and I'm just looking to be pointed somewhere to start, whether it's adding Chemdraw images to pages without them or filling out the red links on the list of inorganic compounds. Reconrabbit (talk) 01:19, 30 November 2023 (UTC)Reply[reply]

If you've just starting editing then I would suggest discreet small molecules to start with. They can be broken down into obvious sections (chembox, lead, synthesis, structure and properties, reactions etc) and cover all the key areas of editing. You could start from scratch or improve one of our stub articles - perhaps propyl gallate, that page is fairly basic but you've probably eaten some of it this week. I would stay clear of things like pesticides unless you have skills in understanding all of the toxicity issues, ditto medicines where we have very high standards for sources. We discourage people from citing their own work, but it is still good to start with what you know. Smokefoot is correct, our numbers are few, I would estimate the global pool of regular chem editors for the English language pages to be no more than 20. --Project Osprey (talk) 01:33, 30 November 2023 (UTC)Reply[reply]

There are several backlogged queues of requests for chemical diagrams. Someone with chemical knowledge and a copy of ChemDraw could make a bunch of contributions without having to dedicate a large amount of time to lit research or learning too many subtle details of WP writing. DMacks (talk) 19:22, 30 November 2023 (UTC)Reply[reply]

I recall seeing that list of requested drawings but haven't been able to find it again. Do you have a link? It might be more helpful to start on the drawings that don't exist yet over the ones that just need to have a .SVG format. I previously had academic access to ChemDraw but don't know if it's still valid - using BIOVIA Draw right now. Reconrabbit (talk) 19:35, 30 November 2023 (UTC)Reply[reply]

They are tracked in several different places:

• Category:Chembox articles without image
• Category:Infobox drug articles without a structure image (though many are proteins or other non-simple macromolecules)
• commons:Category:Low quality chemical diagrams and its /expired subcat (many of these are chemically deficient, not just looking for SVG to replace a high-quality PNG)
• commons:Category:Disputed chemical diagrams and its /expired subcat (substantive factual concerns)
• Wikipedia:WikiProject Chemistry/Image Request (no longer actively used)

DMacks (talk) 19:48, 30 November 2023 (UTC)Reply[reply]

There are established guidelines for drawing chemicals, so in theory the drawing package shouldn't matter too much wikipedia:Manual of Style/Chemistry/Structure drawing--Project Osprey (talk) 22:14, 30 November 2023 (UTC)Reply[reply]

Definitely true. Some are better/easier than others to actually implement that MOS. I only mentioned CD because it's one of the ones that's better at it (at a ridiculous cost!), and what Reconrabbit specifically mentioned in their original post. DMacks (talk) 22:29, 30 November 2023 (UTC)Reply[reply]

@Reconrabbit I use BIOVIA Draw all the time, with Inkscape to convert its .emf image exports to .svg format. Ping me to your Talk Page if you have any issues doing the drawings. Note that our MOS linked by Project Osprey recommends using ACS document settings. My efforts are on Commons here. Mike Turnbull (talk) 11:20, 1 December 2023 (UTC)Reply[reply]

((ChemID)) is a CASNo lookup in the ChemIDplus database, which just appears to be PubChem. There are only a few dozen transclusions (Special:WhatLinksHere/Template:ChemID), all the articles being "chemical" or "drug" articles that would have pubchem ID in the infobox as standard. The ChemID is instead (from spot-checking) listed in External links, and I don't see the value of highlighting that reference (or leading readers to think it's something other than pubchem). Should we get rid of these uses, and then kill the template?

@Leyo: who created it (but obviously anyone is welcome to contribute to discussion!). DMacks (talk) 02:49, 25 December 2023 (UTC)Reply[reply]

It's too bad that ChemIDplus was migrated into PubChem. In cases, where the template is just listed in the External links section, it may just be removed. However, it is also used as a reference to specific infobox values. In Hyaluronic_acid#cite_ref-ChemIDplus_1-0 for instance, the template could be replaced by a link to https://pubchem.ncbi.nlm.nih.gov/compound/3084049#section=Acute-Effects&fullscreen=true that contains the same information as originally the ChemIDplus entry. --Leyo 22:32, 27 December 2023 (UTC)Reply[reply]

I nuked the loose ExtLinks. DMacks (talk) 12:06, 30 December 2023 (UTC)Reply[reply]

All article-space fixed. DMacks (talk) 02:07, 1 January 2024 (UTC)Reply[reply]

Thanks. Unfortunately, there are many more, just without that template: Special:Search/insource:chemidplus --Leyo 19:38, 1 January 2024 (UTC)Reply[reply]

Crikey, 162 in [mainspace articles alone:( DMacks (talk) 03:33, 2 January 2024 (UTC)Reply[reply]

I know. I removed the (relatively few) occurrences in the External links section. --Leyo 20:29, 3 January 2024 (UTC)Reply[reply]

Nomination for deletion of Template:ChemID

Template:ChemID has been nominated for deletion. You are invited to comment on the discussion at the entry on the Templates for discussion page. DMacks (talk) 13:31, 1 January 2024 (UTC)Reply[reply]

Template:Alfa

This template also has a similar problem. The website is moved, and they have changed catalog numbers of chemicals. --Nucleus hydro elemon (talk) 07:40, 8 January 2024 (UTC)Reply[reply]

@1234qwer1234qwer4: Seems like questionable cat, in part because it will cover a lot of topics and in part because few really care. --Smokefoot (talk) 14:02, 25 December 2023 (UTC)Reply[reply]

cover a lot of topics can presumably be solved by subcategorisation, and few really care does not seem like a policy we have? What about the other categories like Category:Substances discovered in the 20th century etc., created in 2018 by @Leiem? 1234qwer1234qwer4 15:05, 25 December 2023 (UTC)Reply[reply]

Seems a reasonable part of Category:Science by century. One could argue whether this is a defining characteristic of each substance. But it does seem like there is widespread (i.e., other fields of science) use of this overall tree, so I don't think chemistry should reject it on our own. If someone(s) care enough to maintain it, that's up to their use of their time. DMacks (talk) 05:42, 26 December 2023 (UTC)Reply[reply]

 You are invited to join the discussion at Talk:1,1'-Bis(diphenylphosphino)ferrocene#Requested move 4 January 2024, which is within the scope of this WikiProject. DMacks (talk) 19:43, 4 January 2024 (UTC) DMacks (talk) 19:43, 4 January 2024 (UTC)Reply[reply]

There is a requested move discussion at Talk:Mitomycin#Requested move 31 December 2023 that may be of interest to members of this WikiProject. SkyWarrior 16:43, 7 January 2024 (UTC)Reply[reply]