User talk:Project Osprey

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Chembox assistance

Howdy! Based on some of the templates you have recently edited, I'm hoping you might be interested in helping me out with a project. I'm working on building a {{Infobox}} based replacement for {{Chembox}}. I have a working proof of concept at {{Infobox chemical}}. Looking for some expert opinions and feedback. If you have any interest, please let me know. Feel free to disregard this message. :-) (P.S. Happy thanksgiving if you are in the USA!) --Zackmann (^{Talk to me}/_{What I been doing}) 19:17, 22 November 2018 (UTC)

Honestly I don't even think I'm qualified to help. I have used chembox a lot but I'm not a template editor and really have no idea how its innards work or how to change them.--Project Osprey (talk) 14:40, 23 November 2018 (UTC)

Phosphorylation etc

I am uncertain if other editors are interested in questions about phosphorylation. So I am relocating my comments to here. My take:

• phosphoryl group = -P(O)X₂
• phosphonates = RP(O)(OR')₂
• phosphates = P(O)(OR')₃
• phosphorylation = the attachment of -P(O)X₂ to amines and alcohols
• phosphonylation = the attachment of -P(O)X₂ to carbon
• hydrophosphonylation = the addition of H-P(O)X₂ across C=X bonds to give phosphonates (X = C, N, O, ...)

What do you think?--Smokefoot (talk) 20:11, 18 February 2019 (UTC)

Thanks, I'd broadly agree with those descriptions. I don't think I did a good job of explaining myself before but my issue was that our current definition of phosphorylation would incorporate hydrophosphonylation. That doesn't seem right to me and the literature certainly doesn't describe things that way. The obvious answer would be to change the definition of phosphorylation to your (and indeed IUPACs) version. --Project Osprey (talk) 00:04, 19 February 2019 (UTC)

The precise definition of phosphorylation also bothers me. The reading about (EtO)2POCl (thanks for the addition, BTW), author refer to its alkylation as phosphorylation when it perhaps should be called a phosphonation. So I guess that the addition of R2P(O)-H across C=O or C=N bonds is hydrophosphonation, I dont know what R2P(O)-H across C=C is anymore. --Smokefoot (talk) 01:51, 19 February 2019 (UTC)

I think that's still a hydrophosphonation; you're still generating a phosphonate. The lexicon of organophosphorus chemistry is often non-obvious, even to chemists, and I think some people are using phosphonylation as a convenient general term for anything that adds a phosphorous-species, like with oxidation or chlorination.--Project Osprey (talk) 11:28, 19 February 2019 (UTC)

Neodymium fluoride

While you're fixing up the article, "violate solid" looks like a typo to me, but I know sweet FA about chemistry. Cabayi (talk) 12:00, 22 February 2019 (UTC)

Nice catch. I can spell all the fancy words but colours are too hard for me. --Project Osprey (talk) 12:20, 22 February 2019 (UTC)

Thanks. Once the word "volatile" had popped into my head the change to "violet" no longer seemed so straightforward. Cabayi (talk) 12:26, 22 February 2019 (UTC)

Triacetonamine

You seem to have an affinity for these compounds, so I wanted to let you know that I merged an article that you helped with into Triacetonamine. Its a more contracted name but I formed the opinion that it is more common term. I actually created this thing today in a frenzy, having forgotten that I had created it under a different name. I am trying to piece together the chemical infrastructure related to TEMPO and its analogues. In any case, fair warning and warm invitation to take a look, revert, complain, etc. I hope things are well over there. --Smokefoot (talk) 02:00, 18 April 2019 (UTC)

Well the big reveal is that I currently work for a company that produces polymer stabilizers. I've not worked with HALs myself but my understanding is that their synthesis is hard, despite the cheap starting materials. Poly-condensation reactions of acetone with ammonia can generate all manner of gunk, muck, resin and tar. Plant production of triacetonamine requires the input of many a chemical engineer. I'll try to have a look at the pages and see if there's anything I can add. Do you have a particular outcome in mind?--Project Osprey (talk) 09:37, 18 April 2019 (UTC)

I have no plan aside from just setting up these articles. Just checking that the revamped article is ok. --Smokefoot (talk) 11:23, 18 April 2019 (UTC)

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Polonium hydride

Hi, I am wondering whether the information you removed in this edit is truly nonsense. I agree that the cited reference is many decades old, and so maybe there are newer, more accurate works which invalidate this old statement. But I am not familiar with this field at all, and so in general can imagine polonium and nascent hydrogen yielding the hydride. Szaszicska (talk) 23:44, 2 August 2020 (UTC)

The issue is that nascent hydrogen doesn't exist --Project Osprey (talk) 22:13, 3 August 2020 (UTC)

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InChI and inorganics / organometallics

Hi, The thread where we were talking about this has become muddled, and is difficult to read because people are not indenting properly.

I wanted to clarify some background as you are clearly interested. As you know, I worked for Syngenta (and ICI / Zeneca before that) at Jealott's Hill. In the 1980's ICI (at that time a corporate effort), with key players from Pharms and Ag Chem (me + IT folk), tackled the issue of moving from WLN to MDL's MACCS connection-table in our company-wide database of compounds, then called CORCCC for "Core Company Compound Collection. The main drive for this, the key User Requirement (a term I'll come back to), was to allow substructure search over the whole collection by end-users sitting at the PC on their desks. This may sound like a minor issue by 2020 but believe me, in the mid 1980s was a big deal and cost a substantial amount of time and effort to implement on VAX machines running at Alderley Park. My single most important (in the long term) contribution was to work out how to handle tautomerism: all users ever saw in the database was 2-hydroxypyridine and never 2-pyridone. Moving on, by the early 2000s we had demerged from (then) Zeneca and had merged with the Ag Chem part of Novartis, forming Syngenta. Novartis itself had components from Ciba-Geigy and Sandoz Ag. They had a huge corporate database but it was entirely reliant on SMILES in the underlying relational db. So a huge debate ensued which was like a Wikipedia edit war. The User Requirements were pretty clear: chemists wanted to merge the major databases and be able to search across the whole of what Syngenta had. Also, at that time we were increasingly purchasing chemicals from third-party suppliers (often Combichem outfits) and we wanted to build on what a system called CAOCI had provided. This was a Currently Available Organic Chemicals Index: first created as a collaboration between ICI and MDL, with MDL numbers (still in use today) as the main business key. So, a tall order: a system that we estimated might grow to hundreds of millions of compounds in a single Syngenta in-house database, well curated and with Business Rules to tell chemists how to input their structures. In the end we got there — and then some academic group invented InChI.

That's the preamble. The bottom line is that InChI is fantastic for future databases of organic chemistry BUT it does have limitations. If your User Requirements are for a Pharma or Ag Chem organisation, then you'll be fine and will trade off the 0.01% of case where it fails. If your users are polymer scientists you will compromise, perhaps. 99.9%+ of polymers are going to be impossible to describe in totality: the InChI string would clearly be too long! So, you would I guess elect to store the InChI for the monomer, and build a schema where block co-polymers were defined in a substance-from-substance way, with extra fields for average molecular weight and so on.

As an organometallic chemist your User Requirements would likely find InChI very acceptable, as the cobalamin case shows. That one, and 95% of others, works because you know the connection table and there's likely to be only one or two metals per molecule. Even iron cluster compounds and boranes are fine as the connections are in principle known. As an inorganic chemist with User Requirements around non-carbon-containing compounds you'll find that InChI's stutter once you go beyond the requirement to allow the molecular formula to stand as the representation: the Fe2O3 → 1S/2Fe.3O idea. The limitations can be seen in the simplest cases. Sulfur is fine if you want the InChI for S8 but fails otherwise (see its Chembox). Similarly Phosphorus — whether you want red or white the InChI as such can't help you. Likewise humble carbon, the true test case for if your User Requirement includes all of chemistry. Where to handle graphite, diamond, Buckminsterfullerene? The last one is fine because we know the connection table, the others (including graphene) not so much!

So, main question, to you and @Walkerma, Egon Willighagen, DePiep, and DMacks: (apologies if I've missed some) is:

WHAT is the User Requirement for the CAS issue? It is real tempting to leap to solutions before these are hammered out. I know from painful experience that IT projects fail (or go way over budget) if a structured approach including all that "boring" think-before-you-act stuff goes awry. Who even ARE the Users we are discussing? My plea is that a "clean slate" Wiki Project page for this be started and that some sort of Project discipline be applied. That's Walkerma's role, I think: correct me if I'm wrong. Michael D. Turnbull (talk) 14:00, 15 October 2020 (UTC)

Thanks for the follow-up and I'm sorry for the delay in getting back to you. The events of the year have reduced my wiki activies quite a bit. My concern (similar to yours I think) was of problems being baked in from the start. I have also sat-in on poorly conceived IT projects where people have been too keen to start (although nothing on your scale). Many chemists tend to default to 'organic' when you talk about databases of structures but we obviously have to accommodate all sorts of stuff. I had for some reason thought that InCHI struggled with inorganic structures in the same way that SMILES does - so at least I've learned something from this.

As for the User Requirements: Honestly, I haven't a clue. I feel like this might be related somehow to this effort to effectively turn wikidata into a 'real' chemical database. I feels like it's very much to do with wikidata and very little to do with wikipedia, if any of our CAS numbers are wrong it'll be on obscure pages that don't get looked at much, the important stuff is correct. I don't really know what wikidata is for so I can't really help.

BTW are you aware of that there's a chemical structure search engine for Wikipedia? It runs on SMILES strings but I've found it very handy in the past. http://www.cheminfo.org/wikipedia/ . --Project Osprey (talk) 20:32, 17 October 2020 (UTC)

I think that we are (literally) on the same page here and I suggest we use this thread to pose the problems/issues rather than discuss solutions. I wasn't aware of the Wiki search engine: brilliant. My ex-Novartis colleagues would firmly support the use of SMILES in that way: it is more than adequate for searching "small" db like here for chemistry articles which have proper Chemboxes. You only need connection tables and InChI for the really big stuff. Mike Turnbull (talk) 11:54, 18 October 2020 (UTC)

We can do some brainstorming but I think the final list of issues should be posted back into the main page, just so other people can find it in future. In any event I think we need to know more before we can really define the issues in anything other than general terms. Lets start with the nature of this new CAS data, I've asked what it's related to, we can take it from there. --Project Osprey (talk) 16:44, 18 October 2020 (UTC)

Good idea. This thread can just act as an archive of my "rant" — or "plea", depending how others see it! Mike Turnbull (talk) 17:26, 18 October 2020 (UTC)

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GOCE: Plastic recycling

Hello:

The copy edit you requested from the Guild of Copy Editors of the article Plastic recycling has been completed.

Please let me know if you have any questions or concerns.

Regards,

Twofingered Typist (talk) 18:51, 24 July 2021 (UTC)

None I can think of, other than to say thanks for your time and efforts --Project Osprey (talk) 21:03, 24 July 2021 (UTC)

Polymer degradation

Hello:

Just a quick note to confirm the copy edit you requested from the Guild of Copy Editors of the article Polymer degradation has been completed.

Please let me know if you have any questions or concerns.

It's well-written and I think a lay person like myself can follow it without too much effort other than perhaps getting descriptions from some of the linked articles.

Regards,

Twofingered Typist (talk) 20:43, 9 September 2021 (UTC)

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Pyranol

The pyranol article where you commented on the PROD is now subject of a full deletion discussion. Mike Turnbull (talk) 16:46, 17 January 2022 (UTC)

Cheers. --Project Osprey (talk) 17:27, 17 January 2022 (UTC)

(Chemicals) articles having no (Chembox, Drugbox)

I have worked on your User talk:DePiep § Articles with a Chembox not in certain WikiProjects request (from Aug 2021!).

I have three lists:

• 1. Articles HAVING [ {{WikiProject Chemicals}} OR {{WikiProject Chemistry}} ] and NOT HAVING [ {{Chembox}} NOR {{Infobox drug}} ]

14694 A User:DePiep/CHEM2022 has WPchemY, WPchemAL - has no IBchem, IBdrug (14694 A 2022-03-07)

• 2. Articles HAVING [ {{Chembox}} OR {{Infobox drug}} ] and NOT HAVING [ {{WikiProject Chemicals}} NOR {{WikiProject Chemistry}} ]

4958 A: User:DePiep/CHEM2022 has no WPchemY, WPchemAL - has IBchem, IBdrug (4958 A 2022-03-07)

• 3. Articles HAVING [ {{WikiProject Chemicals}} ] and NOT HAVING [ {{Chembox}} NOR {{Infobox drug}} ]

3858 A User:DePiep/CHEM2022 has no WPchemicALS - has IBchem, IBdrug (3858 A 2022-03-07)

Bare numbers (of course, WikiProject templates are on the Talkpage):

Articles HAVING [ {{WikiProject Chemicals}} OR {{WikiProject Chemistry}} ] = 30512 A

Articles HAVING [ {{WikiProject Chemicals}} ] = 19422 A

Articles HAVING [ {{Chembox}} OR {{Infobox drug}} ] = 20765 A

Notes:

{{WikiProject Chemistry}} is very wide, and so adds persons like Dimitri Mendeleev etcetera.

Please make a check for reasonable outcomes yourself (click & check some articles in whichever list, to check your own logic expectations)

These are simple lists. If you think they can be refined: please ask. I owe you something ;-)

DePiep (talk) 14:01, 6 March 2022 (UTC)

I can Move the pages to a better place, for you to edit & use. -DePiep (talk) 14:38, 6 March 2022 (UTC)

• Many thanks. I can't imagine how you owe me anything! List 2 is my target but I think I defined it too broadly, ~5000 'missing' pages is improbably high. Can I refine to:

Articles HAVING [ {{Chembox}} ] and NOT HAVING [ {{WikiProject Chemicals}} NOR {{WikiProject Chemistry}} ] --Project Osprey (talk) 18:56, 6 March 2022 (UTC)

OK, I'll drop {{Infobox drug}} from that list. Order of change: -50%, expected. -DePiep (talk) 20:25, 6 March 2022 (UTC)

having Chembox & not in WikiProject:Chem's

• 4. Articles HAVING [ {{Chembox}} ] and NOT HAVING [ {{WikiProject Chemicals}} NOR {{WikiProject Chemistry}} ]

202 A User:Project Osprey/CHEM2022 - A has (IB Chembox) - A has NOT (T-WPchemicALS NOR T-WPchemiTRY) (202 A) 2022-03-09

The page contains the WP:PETSCAN links to re-run, and for editing.

HTH. -DePiep (talk) 07:20, 9 March 2022 (UTC)

Excellent, thank you! --Project Osprey (talk) 09:52, 9 March 2022 (UTC)

Dry water

Hi Project Osprey

Thanks for reminding me that "dry water" is indeed a thing! However, that particular thing doesn't seem to be what DOI:10.14294/WATER.2021.2 is all about. I have no idea what the samples they have made actually consist of but it includes stuff they claim to have made by dunking cannabis in water and in a revealing discussion, apparently with a referee, that's included after the main text they say We were briefly treating the biological implications of the Xerosydryle existence and discovery in our other papers, suggesting that it may be the matrix of life itself. When the Xerosydryle is dissolved in water, in particular, it shows Circular Dichroism. Future research, not easy to perform, will be devoted to understanding if the right- or left-handed chirality is preferred under certain conditions; this may provide clues to understanding why almost all biologically produced chiral amino acids are left-handed, or about the dominance of the right-handed B-form of DNA. This is so bonkers as to defy comment. Hence the suggestion from Graeme Bartlett and others that we should keep any of their work off Wikipedia. Mike Turnbull (talk) 14:41, 13 June 2022 (UTC)

I did try reading their paper last night, but it was late and at some point I think my brain may have melted. I missed the chemical vitalism bit. Fear not, I'm no Xerosydrylic convert. I meant only that there was a real compound beneath the ramblings. I tried in vain to find a review article on the stuff. It would make a worthy DYK candidate. --Project Osprey (talk) 15:27, 13 June 2022 (UTC)

Electron-rich

Would you please take a look at this draft: User:Smokefoot/sandbox3? It could be accused of OR or even textbooky. No rush. Cheers, --Smokefoot (talk) 18:07, 17 June 2022 (UTC)

This is a tricky one to get right. The term has a very broad usage - pretty much all chemistry really. Who are we explaining it to? I think any normal chemist would understand the term without even needing to think about it, so lets not write for them. Our target audience will likely be very new to the chemistry. So we should be careful to explain what we mean is a high density of valence electrons (for instance: S has more electrons that O, but that doesn't mean that S compounds are automatically more electron rich that O compounds). I think concepts like EDG and EWG should be folded in - because they're describing the same concept in another way. Hope that helps. --Project Osprey (talk) 10:17, 20 June 2022 (UTC)

Revision

Hello there fellow editor! I saw that you had edited the page on Phosgene and commented that "pulmonary irritant seems too mild a description".... I edited and revised that part as I understood your concern for me having written in an underestimating manner about Phosgene's formidable nature in the First World War(considering it is a 4 on the health hazard scale). I believe that your valuable advise has helped me think more rationally while editing Wikipedia pages, and I sincerely thank you for that. Happy Editing! :) E3C4B1 (talk) 18:39, 19 June 2022 (UTC)

Not to worry, we all edit over the top of each other. I once had the misfortune of getting a lung-full of this stuff and I can confirm that it's just god-awful. I still don't think 'irritant' is the right word, tear gas is an irritant, phosgene is toxic. I'd be happy with 'toxic pulmonary irritant' (?) --Project Osprey (talk) 10:43, 20 June 2022 (UTC)

I hope that you did not suffer too much due to Phosgene's hazardous effects on the fragile human body. I also concur with what you would expect to be there, but as the same paragraph starts with "Phosgene is extremely poisonous..", I think that the distinct but related line "highly potent pulmonary irritant" may work as well, as even though its more than an irritant, there happens to be no other better substitute for the word that makes more sense in Phosgene's description. E3C4B1 (talk) 17:52, 20 June 2022 (UTC)

Your GA nomination of Bisphenol A

Hi there, I'm pleased to inform you that I've begun reviewing the article Bisphenol A you nominated for GA-status according to the criteria. This process may take up to 7 days. Feel free to contact me with any questions or comments you might have during this period. Message delivered by Legobot, on behalf of Bli231957 -- Bli231957 (talk) 19:40, 20 June 2022 (UTC)

Check it out

See the new image in endocrine disruptor#Bisphenol A (BPA). --Smokefoot (talk) 12:17, 29 June 2022 (UTC)

Well now, that is state of the badass art, and exactly what the article needed. As ever, many thanks for your efforts. --Project Osprey (talk) 12:39, 29 June 2022 (UTC)

Your GA nomination of Bisphenol A

The article Bisphenol A you nominated as a good article has passed ; see Talk:Bisphenol A for comments about the article. Well done! If the article has not already appeared on the main page as a "Did you know" item, or as a bold link under "In the News" or in the "On This Day" prose section, you can nominate it within the next seven days to appear in DYK. Bolded names with dates listed at the bottom of the "On This Day" column do not affect DYK eligibility. Message delivered by Legobot, on behalf of Bli231957 -- Bli231957 (talk) 18:42, 2 August 2022 (UTC)

I have sent you a note about a page you started

Hello, Project Osprey. Thank you for creating Hexamethoxymethylmelamine. User:Bruxton, while examining this page as a part of our page curation process, had the following comments:

Thanks for the article!

To reply, leave a comment here and begin it with {{Re|Bruxton}}. Please remember to sign your reply with ~~~~. (Message delivered via the Page Curation tool, on behalf of the reviewer.)

Bruxton (talk) 17:02, 31 August 2022 (UTC)

Glutaraldehyde ‎

Gotta be the world's most complicated goop! Thanks for repairing that article's layout. --Smokefoot (talk) 13:31, 30 September 2022 (UTC)

No worries. There are plenty of academic papers detailing their new-and-superior tungstic acid catalyst, but what sort does industry currently use? This I can't determine. --Project Osprey (talk) 14:33, 30 September 2022 (UTC)

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Thanks

Thank you for the link to the F-chem article and thank you especially for the New Year greeting. Your slightly obsessive colleague, --Smokefoot (talk) 16:08, 4 January 2023 (UTC)

@Smokefoot: you do post A LOT, I suspect you may be responsible for a not-insignificant percentage of all the content on this Project. It's impressive, especially as unlike most other content producers on the internet there's no real praise in it. So thank you, for your ceaseless efforts. --Project Osprey (talk) 16:21, 5 January 2023 (UTC)

Polyvinyl chloride

Hi. Thank you for the citation-supported portion of the material you added to polyvinyl chloride. However, you also added some uncited material, including multiple sentences and a table. As I'm sure you know by now, since you've been editing here since 2012, this violates Wikipedia's policies. Please do not add such material without inline citations. Thanks. Nightscream (talk) 16:25, 7 January 2023 (UTC)

@Nightscream: Thank you, I am aware of the rules and I had thought that I'd followed them. The table was referenced in its title caption. Much of the uncited text was already present in the section, I didn't write it (apart from the bit which referred to the table) although stating that price and suitability are considerations when choosing something seemed unlikely to be challenged. --Project Osprey (talk) 18:00, 7 January 2023 (UTC)

@Nightscream: just so you know; I think the table is fine and I'm going to re-add it. --Project Osprey (talk) 17:17, 11 January 2023 (UTC)

I see now that there is a citation in table's subheading, which I had not noticed before. I'm sorry I missed that. Thanks. Nightscream (talk) 18:12, 11 January 2023 (UTC)

That's ok, I just didn't want to end up in an edit war. Thank you for your civility. --Project Osprey (talk) 00:10, 12 January 2023 (UTC)

January 2023

Hello, I'm Zackmann08. Thank you for your recent contributions to Phosphoribosylaminoimidazolesuccinocarboxamide. When you were adding content to the page, you added duplicate arguments to a template which can cause issues with how the template is rendered. In the future, please use the preview button before you save your edit; this helps you find these errors as they will display in red at the top of the page. Thanks! Zackmann (^{Talk to me}/_{What I been doing}) 18:44, 20 January 2023 (UTC)

Spectral information

Hi Project Osprey. I was thinking again about the implementation of your suggestion about using AIST's link for spectral information. As you know, they have about 35k records that are well curated. Now it occurs to me that Pubchem has potentially vastly more records than that, which at face value are probably as valid. For example, pyridine is at this pubchem URL and seems pretty similar to the AIST entry here. So I'm a bit worried that we are trying to implement something that could equally well be implemented just by adding #section=Spectral-Information to the Pubchem URL that is already linked in the chembox. Have you any new thoughts on this before I raise this within our discussion at the Project Page? Mike Turnbull (talk) 21:22, 25 January 2023 (UTC)

I wasn't aware of that (I rarely use pub chem), so thank you for your vigilance. Following the links led me to spectrabase, which is also new to me. I still think SDBS is better because the peaks are assigned to the structure and also because the spectra has been collected by what would appear to be an expert group (I doubt many academics collect their own spectra, it's largely undergrad work). It is not, however, a hill I'd choose to die on. I think we should link to spectral information, but I'm not too fussed about whos.--Project Osprey (talk) 22:01, 25 January 2023 (UTC)

OK, I'm not sure what would be best either but I'll raise it in the main thread so other members of the Project can comment. I wouldn't like to see DePiep going to extreme lengths to implement AIST if there is a simple way to implement something equally useful. Mike Turnbull (talk) 22:07, 25 January 2023 (UTC)

Chain extender

You seem like the type of guy who might know something about chain extenders. If so, I would appreciate your looking at this new article. Its very brief.--Smokefoot (talk) 13:57, 3 June 2023 (UTC)

I am aware of them, but I've never worked with them directly - so I will have to do some reading before I edit. My understanding is that they do increase molecular weight, but that the purpose behind this is rheology control. The only way to increase the viscosity of a polymer is to increase its MW, and this is critical for certain applications such as spinning fibre or creating foams with defined densities etc. Chain extenders are important in PET recycling (a growth area) as even trace hydrolysis during reprocessing can greatly increase the melt flow index. I do not understand the situation in polyurethane, are diols monomers or chain extenders? It's possible the word could mean different things in different polymers (like 'scorch') --Project Osprey (talk) 22:27, 4 June 2023 (UTC)

The topic baffles me a little, but your description of MW control and processibility fits with my reading. Polyurethanes are made from diols and diisocyanates. Then the chain extender is a diamine. Diamines would not interact with the urethane groups, I dont think. And all the R-NCO groups have been wiped out by alcohols... or maybe not. Another counter-intuitive aspect is that the residual functional groups must be few and further the resin must be awkward to combine with the extender.

Yes, I see that PET recyclers use extenders - in my source, it was a dianhydride.

Like you imply, the situation is possibly that people just added various reagents to resins to see if the rheology would improve and when they observed beneficial effects, they call these reagents extenders without detailed knowledge of what they do. Many practical people may use extenders without knowing the chemistry. Cheers --Smokefoot (talk) 14:37, 6 June 2023 (UTC)

My understanding of polyurethanes is limited and mostly concerns foams. I believe these use polyols rather than diols to give a fully cross-linked structure (one giant molecule). The industrial situation is a bit hazy, producers will buy polyol blends from suppliers like Covestro which are intended towards certain applications. I get the real impression that the converters don't fully know what they're buying and the producers don't fully know how their polyols are being used. Obfuscation of how things work no doubt suits the parties involved, as it acts as a barrier to market entry - but it makes wiki editing difficult. The situation in other urethanes is no doubt different. It's a diverse group.

Pyromellitic dianhydride is supposedly used for PET. I'd pick my sources with care here; industry often doesn't work how academia believes. Journal papers can be misleading.

Regrettably, my employer is keeping me very busy at the moment, so I'm limited to 'light' edits. It might be some time before I can grapple with this one. --Project Osprey (talk) 15:30, 6 June 2023 (UTC)

Gramisterol.svg

Thank you for Corrected. I've corrected the error in the svg image, so undo this edit in 24-Methylenelophenol.----Htmlzycq (talk) 02:15, 4 July 2023 (UTC)

Silylgermane article deletion proposal

Hello! You proposed deletion of an article "Silylgermane" I created, because it is not notable. Unfortunatelly, me too spotted the article "Silylgermane" I created might be not notable. Maybe someone will improve this article to be notable. I'll try to repair it, but I'll almost surely fail, so, the article will probably be deleted. Honestly, I don't want to spread non-notable information or even disinformation on Wikipedia, I am worried that I damaged Wikipedia by creating this article. :( Bernardirfan (talk) 04:26, 14 July 2023 (UTC)

Don't panic. Sometime articles are started with the best of intentions but end up getting deleted. It can happen to the best of us. There is a reasonable amount of literature on this substance, but it has a narrow focus on it's gas-phase structure and bonding. It doesn't appear to be important, hence me proposing deletion. If you have strong feelings about it maybe start a discussion at WP:CHEMS --Project Osprey (talk) 09:22, 14 July 2023 (UTC)

Since my article is approved by Wikipedia editors, they consider my article notable, thus important. I noticed there are many very short narrow focus articles on Wikipedia about certain chemical compounds, even hypothetical ones, some of which have only three, two, one and even no references at all, nevertheless, all those articles are approved by editors, thus considering them notable, thus important, and those articles are on Wikipedia for years (e.g., chromium hexafluoride, osmium octafluoride and heptasulfur imide, please don't delete them). Bernardirfan (talk) 07:28, 15 July 2023 (UTC)

I think that the silylgermane compound is an important topic, because it is a compound hybrid between disilane and digermane which are notable (despite the notability issue of "Silylgermane") so I created the "Silylgermane" article as a stub, for readers who need to know that the silylgermane compound exists, with interesting (and dangerous) properties (notable, important properties), and for me or other editors to improve and expand the article in the future and making silylgermane topic notable. I think readers must know the information about silylgermane by noticing my "Silylgermane" article. Maybe I misunderstand the notability on Wikipedia, I will re-read about the notability in creating new articles, so I apologize for possible misunderstanding. Bernardirfan (talk) 07:29, 15 July 2023 (UTC)

I searched on the internet and saw articles talking about many derivatives of silylgermane, organic and inorganic, so it would be interesting for me to expand the article by importing the section about the silylgermane's derivatives into my article. If no other editors (or no significant number of editors) agree to delete my article till the expiration date of 19. July, I will remove your deletion proposal and continue to expand the article (unless I conclude I failed to repair the article, in which case I will let you to decide to delete my article). The same will be true for future deletion proposals. I would like someone to help me expanding this article and making this article notable. Thanks for your reasonable reply. Bernardirfan (talk) 07:29, 15 July 2023 (UTC)

Hello, Project Osprey! I did it! I significantly expanded my "Silylgermane" article by putting new informations and reference links from reliable sources, and I am now strongly convinced that my "Silylgermane" article became notable and easy to handle, because silylgermane has some practical applications in electronics industry (production of germanium nanowires and germanium quantum dots) and is used in research of Si-Ge inorganic and organic compounds, and readers must be free to access knowledge about the silylgermane compound and its derivatives on Wikipedia, why hiding it by deleting my article, I would rather improve the article by expanding it by you, me and other editors, which I just did, thus, I am now strongly convinced the topic of silylgermane is important.

So, please, don't delete my "Silylgermane" article because I will continue to expand and improve it (and, as I see, other editors improved my article as well, and I thanked them), and there are so many articles across Wikipedia that you would possibly consider non-notable and hard to handle, even without any reference at all, and they are still there for years (and please don't delete them, they are interesting and important, at least to me and part of other editors and readers, I expanded and improved some of them and added more data and added reliable reference links). Don't discriminate me as an editor from editors of those articles (I consider those articles notable and easy to handle). So, I removed your delete proposal of my "Silylgermane" article immediately after I improved the article, sorry, no offence. Bernardirfan (talk) 13:52, 16 July 2023 (UTC)

I can see that you're putting a lot of genuine effort in here - but regrettably I'm still not seeing the notability. Sources like chemnet or benchchem don't meet out usual notability guidelines. They're sales and distribution websites, not scientific journals. I've referred the matter up to Wikipedia_talk:WikiProject_Chemicals#Silylgermane, to break the deadlock. I will of course abide by the community consensus. --Project Osprey (talk) 20:31, 16 July 2023 (UTC)

At least you see that I put a genuine effort, thank you. You spotted references of "chemnet" or "benchchem" in the article. I don't know who put them. But other references other editors and I put are reliable scientific journals or reliable sources, like "https://www.google.hr/books/", "Spanier, Edward J.; MacDiarmid, Alan G. (1963). "The Synthesis of Germylsilane from Silane and Germane in a Silent Electric Discharge"", "https://pubchem.ncbi.nlm.nih.gov/", "http://www.chemspider.com/" and "Petrucci, R. H.; W. S., Harwood; F. G., Herring (2002). General Chemistry: Principles and Modern Applications", and even "www.chemnet.com/cas/en/13768-63-3/Silylgermane.html". Some of them are put by other editors. I don't understand why those sources are not notable to you. I (and other editors) did everything we can to improve the article. At least, after deletion, I want the article to be kept somewhere for future improvement (including removal of chemnet and benchchem but keeping the important information from those websites about silylgermane). I don't know why other editors approved my "non-notable" article at the first place at all, they and you contradict yourselves. I'm confused. I am still strongly convinced that silylgermane is an important topic that deserves its own article. I will be sorry that the article with all those knowledge about silylgermane will be simply deleted, rather than repaired and improved. But I agree, let's abide by the community consensus. Bernardirfan (talk) 22:32, 16 July 2023 (UTC)

3c-4e bond

It took me a while to fathom this too. Take PF₅. Focusing only on the axial F's.

• Three MO's to accommodate 4e.
• One bonding MO (2e) includes F_ax-P-F_ax. All orbitals in phase.
• Then we flip the phase of the orbital on P to give an empty level. High E. Antibonding.
• The weird MO has zero contribution from P. The pair of electrons resides equally on F_ax's. This orbital does nothing for the cohesion of the molecule. Just parks e's at the axial sites. In technical jargon, this orbital does shit.

Another simplest case of 3c-4e bond is H-bonding in HF₂^- (a very strong H-bond). --Smokefoot (talk) 01:51, 31 July 2023 (UTC)

Thanks for this. My issue starts with the name: A 3-centre-4-electron bond just sounds like two 2-electron bonds between 3 atoms, which is completely normal. Anyway, let’s see if I’ve learnt anything. In phosphate the first 3 P-O bonds are normal 2-electron bonds. The remaining 2 bonds require the s-orbital (a non-bonding lone pair) to become involved in bonding. There are 2 ways this could happen:

• d-orbital hybridisation: where the energy cost for promoting an electron into the d-orbital is paid back by the stabilisation of additional bonding. This approach is contentious.
• 3-centre-4-electron bond: in which the filled s-orbital on the P combines with half-filled p-orbitals on two oxygen atoms to form a MO. This contains a filled bonding orbital, filled non-bonding orbital (with the electrons largely localised on the O’s) and presumably an unfilled antibonding orbital. I also think of this as a sort of 'split dative bond' with the loan pair donating towards 2 different atoms.

Some questions. All the descriptions I’ve seen for 3c4e bonds are linear, with 180°C angles. Is that a requirement, because phosphate doesn’t have this. How does this compare with phosphorane ylides in the wittig reaction, which are always shown as dipolar. Why would a less electronegative element end up end up with a formal negative charge? Project Osprey (talk) 12:00, 31 July 2023 (UTC)

I dont understand phosphate, sulfoxides, etc either. --Smokefoot (talk) 12:10, 31 July 2023 (UTC)

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Speedy deletion nomination of Tris(chloropropyl) phosphate

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DYK nomination of Trixylyl phosphate

Hello! An article you have been editing –- Trixylyl phosphate –- was recently nominated by another user at Did you know, to be featured on the main page. The nomination has now been reviewed, and some issues with it may need to be clarified. Please review the comment(s) at your nomination's entry and respond there at your earliest convenience. Thank you for contributing to Did You Know! Fvasconcellos (t·c) 02:10, 6 March 2024 (UTC)

P.S. I'm not sure you're even aware of this nomination or interested in having the article appear on DYK, but I do think it would be an interesting addition! Fvasconcellos (t·c) 02:11, 6 March 2024 (UTC)

I wasn't aware - the nomination was created, voted on, and closed while I was asleep. I only created the article yesterday, it's still quite rough. Nice to get some early feedback. Project Osprey (talk) 10:48, 6 March 2024 (UTC)

Polymer additive

If you get a chance, please checkout User:Smokefoot/sandbox#Polymer additive, which is a list of topics copied almost verbatim from three old J Chem Ed articles. I was thinking about creating such an overview, even though I am not an expert. The envisioned article would almost be a disambiguation, directing readers to the more fully fledged articles, most of which exist. Alternatively such a list might be incorporated into polymer or even plastic. --Smokefoot (talk) 17:15, 25 March 2024 (UTC)

I'm mildly embarrassed because this is something I should probably be doing. I have done a table at Plastic#Types_of_additive which might be helpful. I'd stick to plastics rather than polymers, at least to start with. Rubber is labyrinth because they keep inventing new things to put into it but never seem to take any of the old stuff out. Polymer processing aids come in a wide variety of types and the distinctions between them often seem fuzzy, stearates are everywhere. In general I'd be happy to help. I'm working on organophosphates anyway and lots of them are used as additives, so it's all the same to me. --Project Osprey (talk) 20:45, 25 March 2024 (UTC)

What a good start you have. I'm glad that I wrote to you. My initial thought is that rather than creating an article is to funnel more search terms toward that table.

It is also dawning on me that the list could be very long. But maybe it should be rather long. Some additives are really covalently linked like crosslinkers but most are not.

My limited exposure to vulcanization has shown me that these compositions are very complicated, e.g., some inhibit crosslinking and others that speed it up. Thanks, --Smokefoot (talk) 03:44, 28 March 2024 (UTC)

It is also dawning on me that the list could be very long. Well, you're not wrong. The EU has done a mapping exercise which found about 400 additives used in quantities >100 tons pa. For some, like tris(2,4-ditert-butylphenyl) phosphite more than 10,000 tons are used pa (just in the EU). Not exactly rarefied stuff. I have made several starts over the years but I keep getting bogged down in the complexity. Different additives are used in different polymers for different applications, plus the whole area is under a lot of regulatory scrutiny. --Project Osprey (talk) 10:38, 28 March 2024 (UTC)

I have sent you a note about a page you started

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Editor experience invitation

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