User talk:ThunderSkunk

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Welcome![edit]

Hello, ThunderSkunk, and welcome to Wikipedia! Thank you for your contributions. I hope you like the place and decide to stay. Here are some pages that you might find helpful:

Please remember to sign your messages on talk pages by typing four tildes (~~~~); this will automatically insert your username and the date. If you need help, check out Wikipedia:Questions, ask me on my talk page, or ask your question on this page and then place {{help me}} before the question. Again, welcome! StringTheory11 (tc) 22:48, 28 December 2012 (UTC)

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Welcome, but how is this constructive?[edit]

Your recent edits of a technical nature on commodity chemicals have been useful. So I was surprised to see [[1]]. Seems below your standards. All editors can find that kind of generic cruft and insert such into any article. You think that it is important that readers be told to avoid mixing ammonium acetate and ClF3? One can avoid such generic content by simply citing the MSDS which speaks more authoritatively than Wikichem. You have to realize that every chemical article could be inundated by generic warnings. You are probably still feeling your way around, in which case I hope you stick to hard core chem content of the sort that the general public would have difficult time appreciating. Keep up that good work. --Smokefoot (talk) 14:03, 27 December 2013 (UTC)

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Suggestion[edit]

You can ignore this message if you find me annoying. My suggestion is that the hydroquinone synthesis from acetylene is probably better placed in hydroquinone than in acetylene where it might just be mentioned with a single ref. Also, the equation that you drew is not that great (but I am picky) - Fe(CO)5 (or some derivative) is a catalyst, not a reagent. And the way the eq is written, it looks like ferrous carbonate is a product. My guess would be something like this (assuming they use hydrogen as a co-reagent):

2 C2H2 + 2 CO + H2 --> C6H4(OH)2

Probably a "line equation" is better than some elaborate artwork.

The mechanism has been examined pretty heavily. My recollection is that the likely intermediate is something like (p-quinone)Fe(CO)3 (quini. This kind of thing is mentioned in duroquinone. Anyway, my trusty Ullmann's Encyclopedia does not even mention the acetylene route to hydroquinone, so the process never got far in the commercial world. In fact, I am pretty sure that none of the iron carbonyls are really used for anything in the synthetic world, which is kind of a shame.

BTW, if you are looking for inspiration for projects, a great source is http://www.orgsyn.org ("OS"). Free on-line and gives historical info on preps. It is sort of a tradition with Wiki-articles on compounds to briefly mention the very first synthesis. The early volumes of OS are more focused on pretty fundamental important organic compounds (these preps were written before there was an Aldrich), whereas the more recent volumes are more focused on methodology, illustrating the use of all kinds of reagents. Lots of our Wiki-articles on reagents should probably cite OS because the references would be so accessible to readers (vs the usual books and reviews that are the backbone of our work).

If you have particular themes that interest you, I might be able to guide you to some good WP:SECONDARY sources, since I have access to a lot of resources.

Happy editing, --Smokefoot (talk) 19:04, 7 January 2014 (UTC)

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A page you started (3,4-Methylenedioxypropiophenone) has been reviewed![edit]

Thanks for creating 3,4-Methylenedioxypropiophenone, ThunderSkunk!

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You're welcome.

ThunderSkunk (talk) 07:16, 11 June 2014 (UTC)

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Unusual use of the term 'inert'[edit]

The page on LiBF4 is the only one I've ever seen in which HF and BrF3 are referred to as inert; they're only not fluorinating everything in sight because everything involved is in the highest fluorination state already. Would something like 'fully-fluorinated' be a better term to use?

Fivemack (talk) 09:07, 1 October 2014 (UTC)

My 2¢[edit]

Well inert is relative, referring to its lack of reactivity to the reagents in question. I can see how it seems like an awkward though statement. Your suggestion sounds reasonable except for one problem: it gives the reader the false impression that those solvents exclude other potential solvent choices. To quote my reference from page 6... "Fluoroborate salts can also be prepared by the reaction of BF3 with a metal fluoride in a nonaqueous, inert solvent, such as HF, BrF3, or SO2." Perhaps liquified Sulfur dioxide could somehow be mentioned too (with some clever wording)? If you're both concise and comprehensive I cannot see anyone having a problem with such an edit.

ThunderSkunk (talk) 17:50, 1 October 2014 (UTC)

Electrochemical acta?[edit]

Not only a primary ref, it is a 2nd or 3rd rate journal. That paper has been cited 1.5 times per decade (6 citations) You can do better than that. --Smokefoot (talk) 01:43, 10 October 2014 (UTC)

That reference is cross referenced from page 282 of reference #3.... which is the secondary reference I added to this article years ago: Grimshaw, James (2000). Electrochemical Reactions and Mechanisms in Organic Chemistry. Amsterdam: Elsevier Science. pp. 1–7 & 310. ISBN 9780444720078.

What do you want from me? A dual citation? Perhaps a social campaign to instill into the minds of every practicing O-Chemist a deeper appreciation of electrosynthesis? Or perhaps I needed to do that 32 years ago? Vague shaming does nobody any good.

ThunderSkunk (talk) 02:38, 10 October 2014 (UTC)

The concern is WP:UNDUE. Not sure the meaning of the remarks about "social campaign ... needed to do that 32 years ago," We all make mistakes and cite stupid stuff occasionally, so dont get hung up by this lapse, learn from it.--Smokefoot (talk) 13:42, 10 October 2014 (UTC)


An appropriate response to poor citations[edit]

Wikipedia has tools for identifying lackluster sources for edits. Check out this page for tagging advice. Template:Verify source Don't you think that that is a more appropriate response to a journal cited edit with a graphic? The undo button shouldn't be used so lightly.

ThunderSkunk (talk) 03:00, 10 October 2014 (UTC)

Sounds like bureaucratic response to a mistake. Listen, if one wants to cite journals articles and are unfamiliiar with an aera, good sources of citations are Chemical Reviews and Chemical Society Reviews. These are sources of WP:SECONDARY on general topics. Then there are many books. --Smokefoot (talk) 13:42, 10 October 2014 (UTC)

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Me4N+ as a methylating agent?[edit]

It would be useful to find a general ref to support labeling Me4N+ as a methylating agent. Seems like a pretty obscure reaction, most folks use it for its remarkable inertness. But I could be wrong. --Smokefoot (talk) 13:53, 28 February 2016 (UTC)

Response[edit]

Well I don't have a general reference, but I could cross reference two extra primary sources from the paper's introduction, a discovery paper in a German journal "für praktische Chemie" circa 1890 and another source from Journal of the Chemical Society (Resumed), doi: 10.1039/JR9270000997, that discusses how the 2008 authors came about their synthesis... Doesn't really seem to provide the level of review/proof you're after though.

Anyways, I see what you're saying but I also don't see these categories as being split into degree's of applicability or popularity. That is, I don't ask myself "Is article X a really good example of category Y?". Rather I ask myself "Does article X imply in some way, however obscure, that it fits in category Y?".

For example, iodomethane can be said to be "induced to serve as a methylation reagent" with a base in a reflux condenser using williamson ether synthesis. However, it's popularity and a qualifying the statement like that makes no difference to me. What I think matters is this, iodomethane methylates using a set of reaction conditions and Me4N+ also methylates using a set of reaction conditions.

So I am not gonna undo your edit because I see your reasoning, but I also don't agree with it.--ThunderSkunk (talk) 19:46, 28 February 2016 (UTC)

Hi there. I realize that I can come on kinda strong (one of the unfortunate personality flaws that comes with my profession), so thanks for not rejecting my suggestion. I always cringe when I make a "suggestion" to other editors.
I realized as I pondered, that some ammonium salts may be methyl transferases, in a biocontext. So we arent done yet with Me-quats! The reason that I jumped on the Me4N+ thing is that the isolation of anhydrous Me4N+F- was a minor triumph in my area of chem, it is the first and possibly only naked fluoride-quat salt out there. With longer chain alkylammoniums, e.g. Bu4N+ Hofmann elimination sets in, and tetraarylphosphonium fluorides are covalent, I think. But the Me group is immune to that problem.
BTW, really great work you are doing with all the Org Rxns and Org Syn citations/descriptions. --Smokefoot (talk) 23:20, 28 February 2016 (UTC)

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Alkynylation[edit]

You did a lot of work on this page. If you think that I messed up, trampled your good insights, or took it in a ill-advised direction, please let me know. I can be maniacal but am also thick skinned. --Smokefoot (talk) 03:33, 1 May 2017 (UTC)

Nah,I am not upset at all. You did a nice job merging the content from the older version of Acetylide into the article. Thanks, good work.

ThunderSkunk (talk) 03:51, 1 May 2017 (UTC)