Talk:Trifluoromethanesulfonic acid

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Suggestions[edit]

Some figures were incorrect, so I deleted them. TFA in place of HOTf, etc. How is HOTf purified? How is the hydrate dehydrated? How to make Tf2O, the anhydride? Check Inorg Syn for MOTf's.--Smokefoot 20:15, 5 March 2006 (UTC)

Acid Type?[edit]

Is this a brønsted acid or a lewis acid? It does have a proton but as OH, suggesting it could be either one depending on the nature of its disassociation. AeoniosHaplo 15:21, 21 April 2007 (UTC)

It seems as if it is a Brønsted acid because it's likely that the proton dissociates. The trifluoromethane acts inductively to draw electron density away from the sulfonic region. The two double-bonded oxygens are also electron withdrawing, making the sulfur atom partially positive. Because of these additive effects, a negative charge on a deprotonated oxygen can donate some electron density to the sulfur atom, thus stabilizing the conjugate base. A stabilized conjugate base indicates the initial acid is rather strong, which is the case here. --Heymon32 23:35, 25 April 2007 (UTC)

It's a Bronsted acid. It is superacidic because it forcibly donates its proton to otherwise nonbasic mediums. Chemguy2 01:19, 3 August 2007 (UTC)

"The triflate anion is immune to attack by even strong nucleophiles."[edit]

Is this supposed to be "electrophiles"? After all, the triflate ion carries a negative charge (excess of electrons). I would say that the fluoroborate ion, another ion derived from a strong acid (HBF4) can co-exist with very electrophilic cations. 38.113.178.13 (talk) 00:31, 10 April 2008 (UTC)

pKa of Triflic Acid[edit]

There is no consensus for the pKa of Triflic acid in water.


Another source suggests a pKa of -13.6 (http://www.armourassociates.com/papers/triflic.pdf (Encyclopedia of Chemical Technology, 4th Edition, Vol. 23, p. 195)).

and Pubchem simply says "~ -15" https://pubchem.ncbi.nlm.nih.gov/compound/Trifluoromethanesulfonic_acid#section=Top

So maybe a range should be presented with multiple citations instead of an exact value. — Preceding unsigned comment added by Marco0126 (talkcontribs) 19:59, 14 February 2017 (UTC)