User talk:Smokefoot/TalkArch2020

Tantalum(V) chloride

Hi Smokefoot, I see that you marked my edits with hazmat/safety information as spam. I'm looking for official guidance on what can and can not be used in terms of external links. I see multiple pages where other vendors provide links not only to the actual documents of safety data sheets but actually to their product pages and we didn't add any promotional data. For example, https://en.wikipedia.org/wiki/Tantalum(V)_ethoxide has links to commercial sites of three vendors. We only meant to provide meaningful and helfpul information and tried to follow and replicate existing practices (I can bring tens of other pages like that with links to commercial sites). Moreover, the links are created with the nofollow tag automatically so not sure why our posts were marked as spam. Please advise on what the correct approach should be and we'll comply with the guidance. — Preceding unsigned comment added by Rytrom (talk • contribs) 03:59, 6 January 2020 (UTC)

Thank you for your note.

1. Wikipedia does not offer advice to its readers (or should not). I think that the rules are here: WP:NOTADVICE or WP:NOTMANUAL. Safety notes should refrain from telling readers what they should and should not do, wear, etc. Wiki presents facts.
2. See Wikipedia:Manual of Style/Chemistry#Safety. In the Chemistry project, articles usually do not have a Safety section unless the chemical is extraordinary: cyanide, strychnine, nerve gas, etc or the chemical is common/pervasive, e.g. vinyl chloride, hydrazine, household stuff, etc. TaCl5 and Mo(CO)6 are pretty specialized chemicals.
3. I guess one could spoon out some TaCl₅ and rub it into one's eyes or skin, but we cannot protect morons from themselves. We also do not tell readers not to hit themselves with hammers.
4. If it seems that acompany is using Wikipedia as a publicity platform, such behavior is probably inappropriate. If you are keen to help users of chemicals, please consider the comments above. In general, editors are triggered by any editor who repeatedly cites a company/institution/author. That is the reason for my accusation of spamming.

• I have no standing in Wikipedia, aside from being an active editor. You might elevate your question to Wikipedia talk:WikiProject Chemicals. There you would get a more official (consensus-guided) response better grounded on official policy. With best wishes, --Smokefoot (talk) 12:04, 6 January 2020 (UTC)

Smokefoot, thanks for the references. It does help and I agree that TaCl5 is not the most dangerous product. What I'm seeking to hear from you (as one of the most active chemical editors) is an approach that is consistent with the wikipedia approach and doesn't discriminate our company against others. For example, in the tantalum ethoxide link that I mentioned before there is a footnote to the "hazard" group of the parameters to a vendor site. Right under it there is a "External MSDS" link pointing to another vendor site. If it is acceptable and we can add such a link to TaCl5 and other products it will solve our issue. Please advise. — Preceding unsigned comment added by Rytrom (talk • contribs) 17:20, 6 January 2020 (UTC)

Dear Rystrom: I confess that I dont know answers to your question so I am going to reproduce our conversation and maybe get something entered into our manual of style. --Smokefoot (talk) 22:59, 6 January 2020 (UTC)

Your intention is not to improve Wikipedia articles but to spam. --Leyo 23:25, 6 January 2020 (UTC)

Leyo, I see where you're coming from but it is subjective. The reason of my question is that there are many compounds that don't exist today in Wikipedia and we're considering adding them. However, being a commercial company we expect to create some links to our product pages. Trying to find an appropriate and not-discriminating way of doing it (as you can see it is not right now with the page that I brought as an example). — Preceding unsigned comment added by Rytrom (talk • contribs) 00:01, 7 January 2020 (UTC)

[Rh(CO)2Cl]2

What is the problem with the addition the E and C analysis with [Rh(CO)2Cl]2 ? — Preceding unsigned comment added by Golfpro996 (talk • contribs) 14:45, 2 February 2020 (UTC)

@Golfpro996: Wikipedia is not a mechanism for one to cite one's own papers or those of one's friends. That behavior can appear self-absorbed, and it does not further the cause of Wikipedia. And it is against the COI rules. If you want to broadcast your papers and those of your friends, then you might start a blog.

There are 2900 articles on [Rh(CO)2Cl]2. Should we aim to cite most of these? Probably not. Or maybe the 700 papers that have appeared in the previous 10 years? Probably not again. So why should we cite your specialized reports? Because you want to help readers? Or help your legacy and that of your pals? The reports you cite are not even widely cited (not in top 100). The parameterization that you refer to is niche. Please, then, try to keep the citations rather general and just avoid COI. Textbook or reviews are our mainstay. We could really use a skillful chemistry editor, but editors must be able to take a broader perspective.--Smokefoot (talk) 14:59, 2 February 2020 (UTC)

Hello, Smokefoot. You have new messages at Nwbeeson's talk page.
Message added 20:17, 9 February 2020 (UTC). You can remove this notice at any time by removing the {{Talkback}} or {{Tb}} template.

Entertainment

While we're on the topic of entertaining chemistry I was particularly amused by this recent paper doi:10.1021/acs.inorgchem.9b03563. Absolute top marks for the image - the paper has nothing to do with cows or radioactive milk but if you saw it you'd definitely pause to read the abstract. --Project Osprey (talk) 01:18, 20 February 2020 (UTC)

EMACs

I did not understand your message about EMACs. In my changes I preserved the name and the abbreviation. While chemists who work on them may call them just "EMACs" or "extended atom chains", that is not a suitable name for the more general readers, including chemists of other persuasions; adding "cluster" is the least that is needed to make the name suitable for them.
(And the article name must be singular, by general wikipedia tradition. The singular also makes the definition more clear.) --Jorge Stolfi (talk) 00:48, 2 March 2020 (UTC)

Thank you for the message. Now we are talking. The starting point is that Peng and Cotton, call these chains EMACs. They invented the acronym and the name. Probably some sort of ego-thing, but that does not matter. It is the jargon that chemists (about a grand total of 20 in the world, perhaps) call these things. There are other sorts of one-d materials aside from EMACs. A book series by Joel Miller describes them. Linear chain compounds are one example for which Wikipedia has no article. Examples: Krogmann's salt and Magnus's green salt, they might be of interest.--Smokefoot (talk) 01:11, 2 March 2020 (UTC)

We have been through this before. Wikipedia is not meant to be written specialists. An article should not be written and named according to the jargon of the few specialists who work on that topic. At the very least, the contents and name should be appropriate to anyone who has basic knowledge of chemistry, and may run into the name somewhere. "Extended metal atom chain" does not make sense for anyone who does not already know what they are. --Jorge Stolfi (talk) 17:16, 2 March 2020 (UTC)

EMACs is established terminology for a fairly narrow set of compounds. Anyway:

1. what makes you think that you have the insights to rewrite history, create new definitions?
2. who are these readers who want to know about EMACs and coincidentally are unfamiliar with advanced inorganic?

I can see that you are being well-intentioned but the idea or replacing established jargon with your own jargon seems wrong. Should we rename condensation reaction to bond formation with release of water because condensation does not make intuitive sense to the average reader who knows no chemistry? Hard and soft acids and bases to Theory of the influence of atomic polarizabability on bond strength?

We dont want to get into rewriting history because the editor after you might not be so enlightened or so generous in intent. Following your policy that we relabel articles for some semi-arbitrary readability, the next editors might be trolls who want to rewrite history, something that is rampant in the world. We could go on and on about this. So I think what you are proposing is dangerous. Admit it: advanced chemistry is, gulp, difficult material. --Smokefoot (talk) 01:18, 3 March 2020 (UTC)

Well,

1. I must insist: a wikipedia article about a subject should not be written for the few specialists who care about it. It should be written for any reader who has the minimum necessary knowledge to understand what the concept is. Thus, specialized jargon -- in the title or elsewhere -- should be used only when really necessary, with definition or wikilink.
2. As for "condensation reaction" etc: That generic target reader does not have to know the common name of the concept (this information, in fact, is the first goal of the article). However, the title of the article must be the name that a chemist would use when trying to communicate with such a reader -- not necessarily the name he would use when talking to his fellow specialists. Thus, the title may have to include qualifiers that the specialists do not normally use among themselves; like "condensation reaction" instead of just "condensation", or "Grignard reagent" instead of just "Grignard".
3. In particular, the title of an article should never be an acronym, but the phrase that the acronym stands for -- even if the acronym is much more used than the phrase, by those who work in the area. Thus the article about the US is titled United States, not US -- which is just a redirect to it. Even because the acronym may have other meanings in other fields that the reader is familiar with. (EMACS happens to be my preferred text editor, for instance...)
4. As for Peng et al and rewriting history: the authors who first described a concept in print do not have any extra "rights" to choose the name of the Wikipedia article about it, or even its definition. There are uncountably many articles whose topics started with a narrow (or wrong) definition that was broadened (or fixed) over time, and with a name that changed over time. If we were to follow that "paternity right rule", the nitric acid article should be titled "spirit of saltpeter" -- in Arabic.

Anyway, take care, and all the best,--Jorge Stolfi (talk) 21:39, 19 July 2020 (UTC)

Atom cluster

You reverted hours of hard work on atom cluster because you did not like something I did. Please. If I misunderstood something (like what was the topic), it was because the article was a big mess, with many contradictory definitons and examples. Before throwing my hard work again, at least take the time to point out my mistakes -- I would gladly correct them. --Jorge Stolfi (talk) 17:22, 2 March 2020 (UTC)

I am very sorry to have caused trouble. You should have announced some intention to rename though. I also have invested a lot in this article, a topic dear to my heart. Notice that I basically agree with your premise, cluster is a big topic. The ones that I am trying to decribe are the compounds, which are not atomic clusters. I will go back and revise and reinstate your wording. --Smokefoot (talk) 01:22, 3 March 2020 (UTC)

Hi, me again. I didn't understand what exactly is your view on that topic now. Seems that you would like two separate articles, one from "chemistry" view and one from "physics" view? What would be the definitions?
All the best, --Jorge Stolfi (talk) 20:49, 19 July 2020 (UTC)

1,6-hexanediol diacrylate

Hi, and thank you for your contributions to Wikipedia. It appears that you tried to give Draft:1,6-hexanediol diacrylate a different title by copying its content and pasting either the same content, or an edited version of it, into 1,6-Hexanediol diacrylate. This is known as a "cut-and-paste move", and it is undesirable because it splits the page history, which is legally required for attribution. Instead, the software used by Wikipedia has a feature that allows pages to be moved to a new title together with their edit history.

In most cases, once your account is four days old and has ten edits, you should be able to move an article yourself using the "Move" tab at the top of the page (the tab may be hidden in a dropdown menu for you). This both preserves the page history intact and automatically creates a redirect from the old title to the new. If you cannot perform a particular page move yourself this way (e.g. because a page already exists at the target title), please follow the instructions at requested moves to have it moved by someone else. Also, if there are any other pages that you moved by copying and pasting, even if it was a long time ago, please list them at Wikipedia:Requests for history merge. Thank you. Robert McClenon (talk) 01:38, 4 March 2020 (UTC)

Well I really screwed that up. I have made the mistake previously and have been similarly reprimanded. My sincere apologies. --Smokefoot (talk) 01:58, 4 March 2020 (UTC)

Copying within Wikipedia requires attribution

Thank you for your contributions to Wikipedia. It appears that you copied or moved text from Sulfite into Sulfite food and beverage additives. While you are welcome to re-use Wikipedia's content, here or elsewhere, Wikipedia's licensing does require that you provide attribution to the original contributor(s). When copying within Wikipedia, this is supplied at minimum in an edit summary at the page into which you've copied content, disclosing the copying and linking to the copied page, e.g., copied content from [[page name]]; see that page's history for attribution. It is good practice, especially if copying is extensive, to also place a properly formatted {{copied}} template on the talk pages of the source and destination. The attribution has been provided for this situation, but if you have copied material between pages before, even if it was a long time ago, please provide attribution for that duplication. You can read more about the procedure and the reasons at Wikipedia:Copying within Wikipedia. Thank you. If you are the sole author of the prose that was moved, attribution is not required. — Diannaa (talk) 14:24, 16 March 2020 (UTC)

I do a lot of editing, and I leave edit notes, some of which are even useful. I move text and figures from article to article as well, routinely. Probably a few thousand cut and pastes. In any case I will make an effort once again to acknowledge such relocations. Thank you for your diligence and advice. Feel free to offer additional guidance. --Smokefoot (talk) 15:25, 16 March 2020 (UTC)

Tetraethyllead

Hi Smokefoot, I am currently working on the extension of the Tetraethyllead article in the deWP and I am looking for the X-ray structure of this compound. I searched Scholar several times with different key words but w/o success. Maybe you can give me a hint where I can find it. Any help is welcome. Thank you. --Mister Pommeroy (talk) 16:16, 27 March 2020 (UTC)

@Mister Pommeroy: It is a liquid so the structure would need to be low T, but surprise! It looks like someone grew crystals of an inclusion complex doi 10.1002/anie.199615471.--Smokefoot (talk) 18:32, 27 March 2020 (UTC)

Perfect! Thanks a lot for your quick reply, it´s much appreciated! --Mister Pommeroy (talk) 18:45, 27 March 2020 (UTC)

Acid Dye

Hi Smokefoot, I have noticed that you edited the 'Acid Dye' article (Special:Diff/929528696/929535248), and wanted to ask for some clarification as to why. As an example, the carcinogenicity paragraph within the description section was almost completely removed. I am a new wikipedia user, and admittedly very inexperienced, so I understand if my edits weren't up to wikipedia standards. It would be nice if I could hear the reasoning behind your edits, so I'll be able to improve on that next time. Additionally, I really feel like you could be a bit more gentle with your words. 'Awful' and 'poor' are not the words anyone wants to hear when they've spent hours on a project that they sacrificed sleep on (regardless of whether or not the quality reflects this) and whilst I apologise for any wrong edit I made, I would also appreciate an apology on the choice of words. I'm sure you understand why it doesn't feel great when someone else deletes the work you have spent time on and doesn't explain why. I would, however, be open to any constructive criticism and would very much welcome that. --PanisaLuengthada (talk) 09:19, 15 April 2020 (UTC)

Various - fiber rayon etc

You asked about help on certain articles on the talk page of 1,2-diaminocyclohexane. Specifically you asked about dyes, polyester and rayon because I work in Dalton. Delighted to help. Lets take the easy ones first. Dyes- very little experience - my colleague handles that side of the business. Only experienced in pigmenting rayon. I wrote this article Courtaulds Red Scar Works Preston where I worked for 5 years as senior shift chemist. I thus have quite a bit of knowledge about rayon. This site was the largest rayon producer in the UK.

On polyester, my current company takes polyester fiber from recovered carpet and chemically modifies is it to produce a recycled polyol so I can help there. Nylon is already recovered and converted back to caprolactam. I have already written articles on epoxy, polyurethane etc but can also help there. Let me know any specific page that needs work please . GRALISTAIR (talk) 22:25, 15 April 2020 (UTC) @GRALISTAIR: you will notice that caprolactam makes no mention of recycling. Please keep up sharing your knowledge. I volunteer to be your stereochemistry consultant! PS there is some talk about bio-derived 1,3-propanediol - real? --Smokefoot (talk) 22:55, 15 April 2020 (UTC)

Serpentinite

		The Geology Barnstar
		Nice changes. Thanks.Akrasia25 (talk) 23:57, 3 May 2020 (UTC)

Thank you. I very much appreciate the recognition. --Smokefoot (talk) 01:45, 4 May 2020 (UTC)

the S-S bond energy

How do you get the value of S-S bond energy? in this edit you said that the S-S bond energy is 265 kJ/mol. Is there are any reference can be verifiable?-- Nanachi🐰Fruit Tea☕（宇帆·☎️·☘️） 09:58, 9 May 2020 (UTC)

Here are some data from the CRC (Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN 0-8493-0487-3. ):

CH3S–SCH3 272.8 ± 3.8 C2H5S–SC2H5 276.6 MeS–SPh 272.0 ± 6.3 C6H5S–SC6H5 214.2 ± 12.6 F5S–SF5 305 ± 21 Hope this helps.--Smokefoot (talk) 15:26, 9 May 2020 (UTC)

• Does the value calculate by (272+272+214+305)/4 ≒ 265 ?-- Nanachi🐰Fruit Tea☕（宇帆·☎️·☘️） 17:24, 9 May 2020 (UTC)

I am unsure of the source of the 265 value, but there is no reason to average the four numbers above. I recommend thta you look around for the BDE for S8. --Smokefoot (talk) 17:54, 9 May 2020 (UTC)

Polymeric structure of PhIO

Hi Smokefoot. It's been a long time! How are things?

I saw you added File:(PhIO)n.png to Iodosobenzene and it reminded me I looked into this structure back in 2016. I looked up your reference, HIJRIC, but saw it has cationic oxygen which will affect the I-O bonding. Carmalt et al., J. Chem. Soc., Chem. Commun. (1994) 20, 2367-2368 (reference #5 in the article) provides some good X-ray powder diffraction evidence that each iodine is coordinated to two oxygens at substantially different distances (unlike HIJRIC). One I-O contact was refined to 2.377(12) Å and the other one was somewhere around 2.04 Å. Hence the dashed bonds in my diagram File:PhIO-polymeric-2D-skeletal.png. Would you consider amending File:(PhIO)n.png to show the asymmetry in I-O bond lengths?

p.s. I did look for secondary sources, but couldn't find anything accessible to me. There are a few textbooks and monographs covering the topic. I found https://books.google.co.uk/books?id=-XkjAQAAQBAJ&lpg=PP6&ots=bw87fZhZ_T&dq=hypervalent%20iodine%20chemistry&lr&pg=PA15#v=onepage&q=hypervalent%20iodine%20chemistry&f=false but the relevant pages (pp. 14-15) are not available in the preview.

Ben (talk) 22:36, 29 June 2020 (UTC)

Hi Ben. Long time, no talk. Nice to hear from you. We did a lot of good work together before your graduate school immersion. I hope that worked out.

Your impact was substantial, dismissing the myths of structural inorganic and PhIO is one that both of us were wondering about, and were both suspicious of the molecular structure for a totally insol material. and you made a nice drawing that should have been put into the chembox vs hidden out of sight.

Yes, you are correct that my image is only an educated guess. But here's my argument. My structure was based on the interior of an oligomer that was capped with a proton or Mg2+ (I forget). A real single crystal result vs powder data, which I assume is superior. The paper (Arnie Rheingold stucture) discussed relevant precedents, one that struck me was PhI=NTs (not in CSD), which has your unsymmetrical structure. I surmized that the asymmetry of PhI=NTs is a consequence of bulk. I could not rationalize why the polymer would undergo such a Peierls distortion unless it is really I=O----I=O (Ph's omitted). One more complication: my feeling/intuition/memory that PhIO is always hydrated, maybe with formula H(PhIO)nOH (where n is large). So the polymeric structure is relevant. --Smokefoot (talk) 01:45, 30 June 2020 (UTC)

I enjoyed those mythbusting days, it was fun working on structural chemistry here with you. I must have decided the PhD needed my attention more than Wikipedia did at the time - probably a good decision as everything turned out well. Glad to be back, now.

I'm not emotionally attached to the PhIO image so I don't mind if it's in the chembox, in the main article or not there at all. The mystery of the structure does intrigue me, though. I get your point about rationalising the available evidence and considering the interior of a polymer makes perfect sense. Ivanov, Popov, Boldyrev and Zhdankin, Angew. Chem. Int. Ed. (2014) 53, 9617-9621 concluded the iodine-oxygen bond in PhIO is an I→O σ dative bond.

To make life simpler for us, it turns out the CSD has an answer on a plate: OYALOR from Wegeberg, Frankær and McKenzie, Dalton Trans. (2016) 45, 17714-17722 is a full structure determination from PXRD of microcrystalline PhIO. It does contain zig-zag I–O···I–O chains with bond-length alternation, but there are also close interchain I···O contacts so you get a corrugated sheet of I and O with phenyl groups above and below. Put another way, I/O layers are separated by back-to-back phenyl layers, much like a lamellar phase. The paper also contains interesting synthetic observations and comparisons with PhIO₂. --Ben (talk) 19:14, 30 June 2020 (UTC)

Okay. Right now I dont have the presence of mind to look into the Dalton Trans and review the artwork. But will be compos mentis in a day or three. Congrats on the PhD. Don't let Wiki-anything interfere with your PhD career. I do worry about Wiki-work being professionally unhelpful, perception-wise. So be careful with this hobby. There is nothing better than real refereed articles. --Smokefoot (talk) 21:19, 30 June 2020 (UTC)

Thank you! Wise words. And no rush on the image - it's just a hobby, after all. --Ben (talk) 08:32, 2 July 2020 (UTC)

p.s. I've uploaded some images of the crystal structure to Commons:Category:Iodosobenzene.

Boranophosphate

Hundreds of papers, you say? Reliable sources discussing this subject in significant detail, as opposed to namedrops? Splendid. All you need to find are two to satisfy the GNG. This time tomorrow, I'll just put in for deletion/merge at AfD, saving their presence, in the article (as opposed to being theoretically out there somewhere). This has gone eleven years without proper sourcing, and it's high bloody time there was some. Ravenswing 13:11, 23 July 2020 (UTC)

Wikipedia has lots of articles that need repair. Some problems have been tagged for decades. Here's the CAS summary "Research Topic "Boranophosphate">references (236)>refine "Book Review" (20)>Nucleoside and Oligonucleoside..." Happy editing. BTW, whats the deal with the threats? --Smokefoot (talk) 13:26, 23 July 2020 (UTC)

Diphenyl ditelluride

Hi Smokefoot,

I came across this reagent recently in lab, and saw our article had its skeletal structure as 90° C–Te–Te angles (File:Ph2Te2.png). Is File:Difenylditelluride.png more realistic? The ball'n'stick and space-filling images are also bent. Do you know if there is any known conformational data (is it really even all-planar)? DMacks (talk) 17:40, 1 August 2020 (UTC)

Let me check. I recall it is a 90° version of H2O2. Ben Mills is back with us, and he probably is quicker on the draw than me. @Benjah-bmm27:.--Smokefoot (talk) 17:44, 1 August 2020 (UTC)

Hi DMacks and Smokefoot, thanks for the ping. I had a look, the angles are roughly 90° (C-Te-Te angles are 97.4° and 100.5°, C-Te-Te-C dihedral angle is 90.8°) and it's chiral which is interesting: Woollins and co, J. Am. Chem. Soc. 2010, 132, 16, 5799–5802. I'll make a new model. --Ben (talk) 17:54, 1 August 2020 (UTC)

Secondary Sources

Hello Smokefoot, you said, that you prefer secondary sources. Do you have some good and recent books for inorganic chemistry/cyanides/isonitrile complexes? Because I look all of my informations up on SciFinder and read journal articles, which shouldn't be the primary source. I would be glad, if you could help me out there. Bosslektorkorrektor (talk) 07:44, 6 August 2020 (UTC)

Indeed Wikipedia prefers secondary sources. Actually the really good sources are WP:TERTIARY = textbooks. Those are the most precious sources.

To find reviews, after the search in SciFinder, filter the hits for "document type" and select for "reviews" and "books". With these, select for those with high citations. Hundreds of reviews exist on MCN.

Many newly published chemists start to edit Wikipedia with the goal of highlighting their contributions. That approach usually leads to frustration because Wikipedia is an encyclopedia (= emphasis on general knowledge). We are not so interested in cutting edge articles. I recommend that editors avoid areas where they publish. Rely on your general knowledge.--Smokefoot (talk) 12:58, 6 August 2020 (UTC)

intro rayon

The article now has two - quite redundant starts for defining rayon (in the topmost, I took the freedom of adding the classification as art silk). This was certainly not intended, or was it? The second one looks like it should start with a definition of viscose, because that's what follows. -- Kku (talk) 09:22, 18 August 2020 (UTC)

Dear Khu: thank you for your help. Feel free to edit widely. Many parallel articles once existed on this theme, and I have been merging and cutting/pasting a lot, so redundancies exist no doubt. --Smokefoot (talk) 12:10, 18 August 2020 (UTC)

Cut shot Aromaticity of porphyrin

Rahulsoman (talk) 18:41, 20 August 2020 (UTC) sir you cut-shot my write up about "porphyrin aromaticity" wrote at Porphyrin Page, please tell me a solid reason. Now I feel the write up is not complete and its not clear to reader. Please see the detailed history bellow. I appreciate you changed the heading into a catchy manner, the rest you damaged the sole of write up.

Porphyrins as Model Systems to Study Aromaticity

In general Porphyrins are macrocyclic molecules that shows aromaticity and follows Hückel's 4n + 2 rule, interestingly upon core modification these porphyrinoid macrocycles can show variable aromaticity.<ref>{{cite journal |last1=Schleyer |first1=Paul v. R. |last2=Wu |first2=Judy I. |last3=Fernández |first3=Israel |title=Description of Aromaticity in Porphyrinoids |journal=J. Am. Chem. Soc. |date=December 3, 2012 |volume=135 |issue=1 |page=315 |doi=10.1021/ja309434t |pmid=23205604 |url=https://pubs.acs.org/doi/10.1021/ja309434t}}</ref> Many scientists got attracted to porphyrinoids because of this variable aromatic behavior, [[Annulene]] chemist Emanuel Vogel synthesised first porphyrin [[isomer]]. This 18pi Hückel aromatic porphyrin isomer is named as porphycene.<ref>{{cite book |last1=Kadish |first1=Karl M. |last2=Smith |first2=Kevin M. |last3=Guilard |first3=Roger |title=The Porphyrin Handbook |publisher=Academic Press |isbn=0123932009}}</ref> Later scientists have synthesized various [[Antiaromaticity|antiaromatic]], [[Möbius aromaticity|Mobious aromatic]] and non aromatic porphyrinoid macrocycles.<ref>{{cite journal |last1=Yoon |first1=Zin Seok |last2=Osuka |first2=Atsuhiro |last3=Kim |first3=Dongho |title=Möbius aromaticity and antiaromaticity in expanded porphyrins |journal=Nature Chemistry |volume=1 |page=113 |doi=10.1038/nchem.172 |pmid=21378823 |url=https://www.nature.com/articles/nchem.172}}</ref>

Smokefoot Changed to

Theoretical interest in aromaticity

Porphyrinoid macrocycles can show variable aromaticity.<ref>{{cite journal |last1=Schleyer |first1=Paul v. R. |last2=Wu |first2=Judy I. |last3=Fernández |first3=Israel |title=Description of Aromaticity in Porphyrinoids |journal=J. Am. Chem. Soc. |date=December 3, 2012 |volume=135 |issue=1 |page=315 |doi=10.1021/ja309434t |pmid=23205604 |url=https://pubs.acs.org/doi/10.1021/ja309434t}}</ref> An Hückel aromatic porphyrin is porphycene.<ref>{{cite book |last1=Kadish |first1=Karl M. |last2=Smith |first2=Kevin M. |last3=Guilard |first3=Roger |title=The Porphyrin Handbook |publisher=Academic Press |isbn=0123932009}}</ref> [[Antiaromaticity|antiaromatic]], [[Möbius aromaticity|Mobious aromatic]], and non aromatic porphyrinoid macrocycles are known.<ref>{{cite journal |last1=Yoon |first1=Zin Seok |last2=Osuka |first2=Atsuhiro |last3=Kim |first3=Dongho |title=Möbius aromaticity and antiaromaticity in expanded porphyrins |journal=Nature Chemistry |volume=1 |page=113 |doi=10.1038/nchem.172 |pmid=21378823 |url=https://www.nature.com/articles/nchem.172}}</ref>

The edit was included under "Potential applications". There is zero application from the aromaticity. See also WP:SECONDARY --Smokefoot (talk) 22:14, 20 August 2020 (UTC)

Are you okey with my chemistry writeups

Dear sir, Its really hard to see that you simply deletes few of my writings. If you notice any problems in my writing. Let me know. Rahulsoman (talk) 08:32, 21 August 2020 (UTC)

information from isomer

Good day Smokefoot, your removal of this information prompts me to think about inclusion of related information. If you were in my boat, would you create a entirely new article, caproleic acid|new article from existing "red" llinks or Decenoic_acid#Free_acids_and_esters|adding the information into a related existing article? -- Ktsquare (talk)

@Ktsquare: Do you understand why I reverted your (clearly well-intentioned) contribution? Your paper makes another decenoic acid, not 2-Decenoic acid. If you think that caproleic acid is notable, then go for it. Its fun to start articles. ChemAbs has about 700 citations to it, which seems to prove notability. Olefin metathesis might be a minor part of the story of this chemical, so keep an open mind. Happy editing.--Smokefoot (talk) 23:21, 2 September 2020 (UTC)

Does this edit count as yours or mine?

Hello Smokefoot, I just added your edit on Redistribution (chemistry) to another article, essentially a copy and paste. I added the source which include your edits according to the page history of the source article, out of courtesy. Wikipedia article history counts the latter edit as mine as my account added the sentences and reference to the latter article. -- Ktsquare (talk) 16:10, 18 October 2020 (UTC)

@Ktsquare: Oh, that kind of accounting is not something that I pay much attention to. I have cut and pasted other's work often, and one or two editors have occassionally reminded me that I should be more careful with attribution. Best wishes, --Smokefoot (talk) 19:53, 18 October 2020 (UTC)

Cresol

Hi Smokefoot - a real blast from the past here. Back in the mists of 2011, you merged some stuff to Cresol from, among other things, 5-methylphenoxy. Specifically, listing Bupranolol and Indo-1 as derivatives of p-cresol. But I just absently noticed that they aren't - as far as I can see those compounds (and indeed anything with 5-methylphenoxy in it) is surely another derivative of m-cresol, not p-cresol, which would be 4-methylphenoxy. I'd have just corrected this, but my days of chemistry structures were quite a while ago and it's been sitting there for nine years, so I thought I'd run it past you and check if you agree it was a mistake! Keep up the good work. ~ mazca ^talk 17:44, 19 October 2020 (UTC)

Oh, thank you for the help. If you see anything else, let me know. Otherwise, I wish you all the best as you recede into the mists again.--Smokefoot (talk) 17:52, 19 October 2020 (UTC)

Polyphenols vs tannins

On my talk page, you said: Hey, I left a small rant on the merge discussion vis a vis polyphenol vs tannin. Be assured that my frustrations are with the topic, not you. I kind of wish that I had more time and more knowledge, but it's a fringe area of chemistry. Articles become v difficult to manage once they take on nutritional or medicinal, esp folksy medicinal/nutritional, aspect. The consequence is that such folk-science topics tend to be as weakly edited as they are heavily consulted by normal people.

There is a lot of misinformation in the public about the health effects of these phytochemicals (blueberries are a 'superfruit' because they contain blue-pigmented anthocyanins; pomegranate juice is an "antioxidant superpower"). Polyphenols are extensively degraded during digestion, and their metabolized subunits are impossible to trace and study in vivo for effects on organs or mechanisms of action. It is a 'fruitless' line of research ;>) because it can never be defined for cause-and-effect. The Oregon State University LPI has a good handle on the overall literature, as their nutritional biochemists have studied polyphenol metabolism and published about it over decades, leading to this conclusion about the weak possible health effects of polyphenols and tannins. For your merger proposal, there isn't much editor interest. You could type notes to individual editors to ask for their opinion on the merge talk page. I think the simplest solution, however, is to close the proposal, not merge, and work together to clarify the articles on tannin and tannic acid. Best to you. Zefr (talk) 16:01, 6 November 2020 (UTC)

terpenes

We're currently cooperating on the terpene article. Ok, enlighten me. Terpenes, being carbon and hydrogen are rather easily defined. Nothing suggests that these can be dissolved in water, and my testy experience suggests that such is a poor procedure. But it depends on who is asking. If a PhD chemist asks, I've seen solubility numbers for water solution, though I can't give you the compound, because I don't remember. A terpene, not terpenoid or terpene alcohol. Are there any? An absolutist statement occurs to me is probably false. What I remember is that a few are very sparingly soluble in water, as in probably if I boil something like cannabis, some stuff will remain dissolved after decanting. Am I stupid? The more complex terpenes will break down under heat and pressure, but go into solution, hmmm... Sbalfour (talk) 01:37, 18 November 2020 (UTC)

When chemists say that something is insoluble, they usually mean very pooly soluble (like 0.1 mg per liter). Tables of solubility data exist, but I dont know of any for terpenes. Now the terpenoids, i.e. terpenes modified by addition of polar groups (OH, C=O, etc), would be incrementally more soluble in water than their terpene counterparts. Typically solubiliy increases at higher temp. And solubility in water inversely scales with mol wt. Diterpenes are less sol than terpenes.

Here is what the "Rubber Bible" Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN 0-8493-0487-3. says about the solubility of alpha-pinene "i H₂O; msc EtOH, eth, chl" meaning insol in water (but 0.0000001 g would probably dissolve in a liter) and miscible with those organic solvents. BTW you will encounter disputes about the meaning of miscible (i,e, solubilty of liquids in one another). Organic chemists rarely are interested in quantifying solubility.

I dont know why cannabis would be mentioned on the page of terpene page. I think in the annals of terpenes , cannabis is unimportant because (a) it is terpenoid, (b) it is minor in abundance compared to pinenes and such, (c) it is super complicated structurally, so little pedagical value (IMHO) unless one is deeply into bio-organic chem.

One more comment: solubility is not important aspect of terpenes (or virtually any class of organic compounds). If you look at an organic text, solubility is not a thing. The big topics for any class of compounds are structure and reactions (super rich theme but complicated), apps (few in the case of terpenes), biosynthesis, biological function (probably antifeedants, if any, ).

--Smokefoot (talk) 10:22, 18 November 2020 (UTC)

/* Fuel */ Response: Added sentence with U.S.patent reference about DME use as blendstock in propane autogas to Dimethyl Ether but it was removed.

Dear Smokefoot, I am a new contributor. Yesterday, I made a contribution to the Dimethyl Ether Wikipedia page regarding using DME as a blendstock in propane autogas. I cited US Patent 5,632,786. You removed this contribution on the basis that "patents are unreliable". I appreciate you're being careful. However, this patent is valid based on it being issued by Amoco Corporation; last week I spoke directly with two of the inventors; currently there are on-going efforts by Suburban Propane and Oberon Fuel in southern California to develop this application. Furthermore, this application has been included in a peer-reviewed paper, Literature Cited: Fleisch, T.H., et.al.,"Introduction and advancement of a new clean global fuel: The status of DME development in China and beyond", Elsevier Journal of Natural Gas Science and Engineering, 9, (2012), 94-107. Please either reinstate my contribution with the later journal citation or allow me to do it. Alternatively, please provide guidance as I would like to be a contributor to this Wikipedia subject. Respectfully, XTLExpert001

XTLExpert001 (talk) 13:34, 19 November 2020 (UTC)

Well the main thing is apologies for making your initial editing effort so miserable. II would be glad to help remedy the situation.

People claim all sorts of stuff in patents. Wikipedia is in the business of disseminating general and highly verified knowledge. General knowledge is vetted and vetted. For this reason, Wikipedia relies on reviews and books for big topics like DME. These sources are typically highly vetted. People seeking super specialized info should go to the tech literature.

Then there is the practicalities. About 3 publications (patent, journal article, govt report) appears per day on DME. So Wikipedia should tell readers that this particular patent demands attention? What about the other 10,333 reports that appeared in the preceding decade? Or the 389 other patents issued on DME in 2020?

So your frustration is understandable, but few people realize the scale of the publications out there.

If you are keen to contribute on the topic of DME here are two WP:SECONDARY-quality sources that are highly cited:

doi: 10.1021/acs.chemrev.6b00816

doi: 10.1016/j.cep.2014.06.007

Dear Smokefoot, Thank you for your prompt response. Being patient and persistent and following your guidance, let me cite the Elsevier article, to support my contribution, which was an Invited Review - certainly at least on par with your example 10.1016/J.cep.2014.06.007. The citation directly from ScienceDirect: T.H. Fleisch, A. Basu, R.A. Sills, Introduction and advancement of a new clean global fuel: The status of DME developments in China and beyond, Journal of Natural Gas Science and Engineering, Volume 9, 2012, Pages 94-107, ISSN 1875-5100, https://doi.org/10.1016/j.jngse.2012.05.012. (http://www.sciencedirect.com/science/article/pii/S1875510012000650) Abstract: The last two decades saw the emergence of a new multi-source, multi-market fuel, Dimethyl Ether or DME. Prior to 1990, DME had only found limited commercial use as an aerosol propellant along with propane and butane as a green replacement for the chlorofluoro-hydrocarbons which were outlawed because of their detrimental impact on the ozone layer. DME is an environmentally benign, non-toxic, biodegradable product with physical properties similar to LPG. Global DME annual production capacity is approximately 10 million metric tons and actual market use is reported to be about 3 million metric tons – a remarkable increase from the 200,000 metric tons market demand in the early 2000s. Nearly all of the DME is produced in China from coal-derived methanol via the well known catalytic dehydration process where two molecules of methanol react to form one molecule of DME and one molecule of water. DME is the fastest-growing methanol derivative, yet is still an emerging business with lots of upside opportunities combined with significant challenges. A number of other DME plants are in different stages of development around the world including Egypt, Middle East and Indonesia, all of them natural gas based. Sweden is the leader in the development of bio-DME produced through the gasification and conversion of black liquor, a byproduct in Sweden's paper and pulp industry. Nearly all of today's DME is used as a blend stock for LPG which in turn is primarily used for cooking and heating. At blending levels below 20 vol %, the existing LPG blending facilities, local distribution infrastructure and end-use equipment can be used with minimal (if any) modifications – making for easy marketing. Currently, efforts are underway to commercialize DME as a high-quality diesel alternative. Technical issues such as new fuel injection systems and new fuel additives have been solved and solutions are currently being tested in fleets. This review will describe the history, status and future of DME as a global fuel alternative and how it has and will be changing the global methanol industry.

On page 2 of this peer-review paper are the sentences- "It was shown that blends of up to 20 vol% DME in LPG worked well in standard cooking and heating applications..... Similar blends performed well in automotive applications and were patented by Amoco (US Patent 5,632,786, 1997). Doesn't this secondary source citation support the inclusion of my original sentence "Dimethyl ether can also be used as a blendstock in propane autogas. Note that I would change my original citation to this Elsevier article.

Also, let me add that I am an honorary member of the International DME Association, and an internationally-recognized expert on DME as a fuel. As such, I believe that I am well qualified to contribute what information about DME that are of value to Wikipedia. Currently there are on-going efforts by Suburban Propane and Oberon Fuel in southern California to develop this application using renewable DME. I remain keen to contribute more on developments about DME as a fuel.

I am respectfully requesting that you approve my initial contribution with the above change in the citation. — Preceding unsigned comment added by XTLExpert001 (talk • contribs) 03:20, 20 November 2020 (UTC) --Smokefoot (talk) 16:55, 19 November 2020 (UTC)

What about the other 300+ patents issued on DME in 2020... should we cite them too? Why not? Because you are not friends with those inventors?

• Easy solution: cite the review that cites the (somewhat narrow) patent.
• Your credentials mean nothing here. Nor do mine. We dont work that way here. Its all about sources and objectivity. Difficult to be objective when one is plugging friend's patent.
• Wikipedia is international, so the goings on in s. California or any particular U.S. state is not necessarily significant.
• I am not in charge here. Best wishes, --Smokefoot (talk) 11:45, 20 November 2020 (UTC)

Dear Smokefoot, I am appealing your decision. I have used the Request Dispute Resolution Notice process by using the Template: DRN-notice/doc, which I have edited and published. As I am not familiar with the Wikipedia process, please advise if I have not used the DRN process correctly. I did not see how I could send a DRN other than using the Template. Please correct if appropriate. Thank you. — Preceding unsigned comment added by XTLExpert001 (talk • contribs) 20:08, 20 November 2020 (UTC)

I know about this because I saw the edits at Template:DRN-notice/doc, which is on my watchlist because I'm one of the founders of the Dispute Resolution Noticeboard. I'm hoping to avoid an unnecessary filing there. Are you both willing to accept this edit if it is cited only to the Fleisch, Basu, Sills paper, without any mention of the patent? Regards, TransporterMan (TALK) 21:30, 20 November 2020 (UTC) PS: I saw the DRN filing after posting this, but have removed it because it was manually done, rather than being done through our listing bot. Manual filings break our maintenance bot at DRN and are not allowed. Please consider the question I have asked, above, before relisting at DRN. — TransporterMan (TALK) 21:39, 20 November 2020 (UTC).

Dear Smotefoot. Yes, I am willing to accept posting of my contribution with the reference of the Elsevier paper without any mention of the patent. Regarding the DRN process, I appreciate your correcting my mistakes first filing using the template and then filing manually. I'm still learning. Going forward, I would appreciate your inputs to my future contributions. Regards, XTLExpert001

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Having an off day?

Hi Smokefoot. I tidied up a couple of oddities you had left in the 1,2,3-Benzothiadiazole article. We all have off days! Mike Turnbull (talk) 16:53, 26 November 2020 (UTC)