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The following is an archived discussion of the DYK nomination of the article below. Please do not modify this page. Subsequent comments should be made on the appropriate discussion page (such as this nomination's talk page, the article's talk page or Wikipedia talk:Did you know), unless there is consensus to re-open the discussion at this page. No further edits should be made to this page.

The result was: promoted by Cwmhiraeth (talk) 06:31, 24 February 2017 (UTC)

DYK toolbox

Trifluoroperacetic acid

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Created by DMacks (talk) and EdChem (talk). Nominated by EdChem (talk) at 13:27, 16 January 2017 (UTC).

  • @DMacks: Any suggestions for a better hook?
  • QPQ required. Nominated just in time for DYK eligibility, and of sufficient length. Assuming good faith for the references I cannot access (5 and 9). The last sentence of the article could probably use a link to methanolysis (or the redirect target transesterification). The sentence fragment "...is usually prepared immediately prior to use..." is probably true, but the ref only gives one example; it does not state this is typical (unless I missed it). Hook is OK and sourced in the article. Aside: I searched for an appropriate WP link to "α,β-unsaturated ester" but could find nothing relevant; is there a suitable target for this, as most readers will not be familiar with the term? (This is not required for this DYK nomination, just a suggestion to improve the article.) I'll review any additional hooks you want to consider; perhaps a hook such as ALT1, as most readers should be familiar with hydrogen peroxide. Mindmatrix 18:25, 16 January 2017 (UTC)
    • Editorial responses: I removed the methanolysis detail. The chemical is not available from Aldrich, a major/comprehensive chemical supplier for research labs, but I'll try to find a direct ref for made-when-needed. I linked "α,β-unsaturated ester" to A,b-unsaturated carbonyl compound, which is a redirect to a specific section of carbonyl group. DMacks (talk) 22:25, 16 January 2017 (UTC)
  • ALT1: ...that trifluoroperacetic acid can be prepared in two different ways using hydrogen peroxide?
I found a comment made in passing that there is a third way from H2O2, will track it down tonight and add what I find. DMacks (talk) 22:25, 16 January 2017 (UTC)
Yup, using an alternate formulation (stable solid) that contains H2O2 rather than H2O2 itself in water. Added, with commentary about significance of this method. DMacks (talk) 03:33, 17 January 2017 (UTC)
In light of recent changes, ALT1 is wrong, so I am striking it in favour of ALT2:
I still need to do the QPQ. In the meantime, I wonder if we can come up with any other alternative hooks? DMacks? FYI, a valid hook starts with "that", has the article name in bold, and has a fact that is in the article and supported by an inline-citation, and a maximum of 200 characters. We want something that is interesting to as broad an audience as practicable. It's a much easier task for the HMB nomination. I've no other parts I'm planning to add at present, by the way. Is there anything else you think is important and missing? EdChem (talk) 12:16, 17 January 2017 (UTC)
I'll wait to review the new additions until you've completed your expansion. Mindmatrix 13:42, 17 January 2017 (UTC)
I just fleshed out the last part I intended to do: intro and expansion of the single example that had been § Oxidation with acidic rearrangement. One or more images still need to be redrawn to WP-MOS standard, will try to get to it tomorrow. DMacks (talk) 04:50, 19 January 2017 (UTC)
For the hook, might be able to make it seem more interesting ("wow, that's a crazy compound") by mentioning that it's too unstable/dangerous to ship but that it can be made easily three ways. DMacks (talk) 04:51, 19 January 2017 (UTC)
I like that idea, DMacks. We'll need to have a reference on shipping hazard, though, but that should be doable. EdChem (talk) 06:19, 19 January 2017 (UTC)
I can't find a cite for it (I don't have access to hazardous-materials encyclopedias). Can the hook be more than one sentence and include more than one interesting nugget?
is just under 200 characters as displayed. DMacks (talk) 16:07, 19 January 2017 (UTC)
No, it can't be more than one sentence, and it must be phrased as a question so it fits the format "Did you know ... that [TEXT]?" Yes, it can have more than one fact / nugget, so long as all are in the article and supported with inline citations. We could consider:
"Potentially explosive" is supported by this book reference (which I have added to the lede and property sections), that it is not commercially available is in the e-EROS source (ref 5), and the three preparations from H
2O
2 are in refereces 2, 5, and 7. EdChem (talk) 01:32, 20 January 2017 (UTC)
Ooh ALT4 is nice! DMacks (talk) 04:17, 20 January 2017 (UTC)
I've amended ALT4 as ALT5, which I think flows better and is slightly more compact. What do you think? Mindmatrix 13:44, 20 January 2017 (UTC)
  • Pinging DMacks and EdChem to comment on ALT5; if they're happy with it, we can proceed. Given that it is a simple rearrangement of ALT4, I don't think there will be any issue if Mindmatrix ultimately approves the hook. BlueMoonset (talk) 06:51, 12 February 2017 (UTC)
  • Thanks for the ping, BlueMoonset. I had been meaning to add a bio on the scientist who pioneered the work on TFPAA, but I haven't got to it and who knows when I will, so I agree this should be moved forward. I have added a hyphen to ALT5 in ALT5a, below, as I think it is more correct, but will stand corrected if I am in error. I have also struck the options prior to these as I agree that Mindmatrix's tweak is an improvement. Apologies for not commenting earlier, Mindmatrix.
DMacks, any thoughts on ALT5 v. ALT5a, and are you happy with the modification in going from ALT4 (which you said is nice) to ALT5 / ALT5a? EdChem (talk) 01:09, 15 February 2017 (UTC)
EdChem, definitely not ALT5a over ALT5: there shouldn't be a hyphen between an adverb ending in "ly" and the word after it that it's modifying. I've struck that variant; glad you think ALT5 is an improvement. BlueMoonset (talk) 07:41, 17 February 2017 (UTC)
I was thinking "potentially explosive" was serving as a an adjectival expression modifying the noun "trifluoroperacetic acid," though "potentially" is also modifying "explosive." Not stressed if I'm wrong, though. EdChem (talk) 14:52, 17 February 2017 (UTC)
  • Comment: I will review the newly-updated article sometime early next week. Mindmatrix 15:46, 17 February 2017 (UTC)
  • @EdChem: Although the acid is likely easy to prepare, source only states "quickly" not "easily". Not needed for DYK, but ref 5, page 627 appears to list toxic effects that could be mentioned in the article (I base this on a "from inside the book" Google search which shows a three-line result, so I could be wrong.) I am assuming good faith for numerous refs I cannot access (the bulk of text from "Heteroatom oxidation" onward). The phrase "The hypervalent compound its conveniently accessible in two ways..." is odd; perhaps replace "its" with "is", and remove the POV statement "conveniently". The sentence "Common cases include iodine, for example, iodobenzene mentioned earlier, nitrogen, sulfur, and selenium" might be better phrased as "Common cases include iodine (for example, iodobenzene), nitrogen, sulfur, and selenium." In the phrase "By contrast, trifluoroperacetic acid typical oxidises...", you probably want "typically". Not needed for DYK, but are there suitable links for "pathway" (the closest I found was Metabolic pathway), "S-oxidation", and "S,S-dioxide". I can't seem to verify the sentence "For alkenes, the reaction gives carbonyl products..." - could you point me to the correct location (page and paragraph/section) in the source to verify this? Should the term "preferentially" link to PROX? Hook is OK and soured, with the exception of the term "easily" as mentioned earlier. Overall, only a few minor issues. Mindmatrix 17:39, 18 February 2017 (UTC)
Quoting your comments in blue for clarity in responding, Mindmatrix:
  • Although the acid is likely easy to prepare, source only states "quickly" not "easily".
It certainly is easy to prepare, essentially by mixing trifluoroacetic acid an hydrogen peroxide, though I recognise that my chemical knowledge is insufficient a source for the assertion. Changed
  • Not needed for DYK, but ref 5, page 627 appears to list toxic effects that could be mentioned in the article (I base this on a "from inside the book" Google search which shows a three-line result, so I could be wrong.)
I can't find this. Can you give me a link?
  • I am assuming good faith for numerous refs I cannot access (the bulk of text from "Heteroatom oxidation" onward).
Much of that content is at least outlined in reference 5, which you can find here
  • The phrase "The hypervalent compound its conveniently accessible in two ways..." is odd; perhaps replace "its" with "is", and remove the POV statement "conveniently".
Yes, it was meant to be "is" rather than "its" – fixed, and also removed conveniently as requested
  • The sentence "Common cases include iodine, for example, iodobenzene mentioned earlier, nitrogen, sulfur, and selenium" might be better phrased as "Common cases include iodine (for example, iodobenzene), nitrogen, sulfur, and selenium."
Copyedited
  • In the phrase "By contrast, trifluoroperacetic acid typical oxidises...", you probably want "typically".
Corrected
  • Not needed for DYK, but are there suitable links for "pathway" (the closest I found was Metabolic pathway), "S-oxidation", and "S,S-dioxide".
S-oxide and S,S-dioxide are synonyms of sulfoxide and sulfone, respectively, both already included in the article with links. S-oxidation just means oxidation of the sulfur atom in a sulfide to a sulfoxide or sulfone. On "pathway", I don't see a suitable target. The content is covered in side reaction, at least somewhat.
  • I can't seem to verify the sentence "For alkenes, the reaction gives carbonyl products..." - could you point me to the correct location (page and paragraph/section) in the source to verify this?
It's in the title of the reference, the carbonyl product is the ketone to which the paper refers. I have made this clearer by using the term ketone in the article text.
  • Should the term "preferentially" link to PROX?
No, it should not. PROX is referring to gas streams where CO is oxidised in preference to H2, and thus CO can be a catalyst poison for a process. In this article, the preferential oxidation occurs when one moiety in a molecule oxidises before another, though both are oxidisable. Benzene undergoes a ring-opening oxidation with TFPAA. Pyridine theoretically can undergo N-oxidation or ring-opening or both, but in practice the N-oxidation occurs first and inactivates the ring sufficiently to prevent the ring-opening oxidation analogous to that which benzene undergoes from occurring.
  • Hook is OK and soured, with the exception of the term "easily" as mentioned earlier.
Struck ALT5, added ALT5b to use quickly instead of easily:
I think that covers everything you have raised, Mindmatrix? EdChem (talk) 14:21, 19 February 2017 (UTC)
  • @EdChem: Your changes look good. I apologize for some of my seemingly novice questions - it has been a very long time™ since I last studied chemistry, and I guess it shows (though "S-oxide" etc should have been obvious to me). Thanks for putting up with me as I've been slowly refreshing my memory. Regarding the toxic effects, I mistakenly said "ref 5" instead of "ref 8" (Hazards in the Chemical Laboratory). A search for "Trifluoroperacetic" yields these "From inside the book" results at Google Books, which doesn't give me enough context to verify that it is this acid being discussed on page 627 (though it's likely given the other details). Thanks also for putting up with the pedantry of "quickly" vs "easily". Good to go for ALT5b. Mindmatrix 16:57, 22 February 2017 (UTC)
@Mindmatrix: I do quite a bit of teaching, and am always happy to explain or help someone who genuinely is interested and trying to understand, and I encourage all questions, so I have no issues with how you have handled this review. DMacks is a relative newcomer to DYK, so I hope he has found the process a useful learning experience and will contribute further articles in time. Regarding the ref 8 link you provided, my google snippet view shows only part of what looks like an index. I have certainly used this book before, but not recently, and I don't have a copy easily to hand for checking it properly. You could make a note on the talk page if you like.  :) Regards, EdChem (talk) 14:24, 23 February 2017 (UTC)
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