Talk:Pyrithione

Acid/base properties
"Pyrithione is a weak acid with pKa values of −1.95 and +4.6 (thiol proton)...but is a markedly stronger acid than either of its parent compounds, both of which have pKa ~ 8.

There is something wrong here. An acid with a pKa<2 is effectively a strong acid. Most probably there is confusion between pKa and pKb values: see Acid dissociation constant. The OH group is weakly acidic and the pyridinic N is basic. pKa of -8 is certainly wrong; it implies that the compound is a strong acid.

I don't like the diagram which appears to show ion-pairs. the Na+ ion is very unlikely to associate strongly with -O- and even less likely to associate with -S-. It may be normal practice for organic chemists to show N oxides in a canonical form with "charges" on N and O, but this is misleading in regard to acid-base properties. Petergans (talk) 11:05, 18 January 2017 (UTC)
 * It does not say a pKa of -8, it says a pKa of the order of (with a tilde, ~) 8. This could be changed to "both of which have  pKa values of around 8" or similar.  The source for the  pKa data is here.  There are two values as the thione form is a stronger acid than the thiol form.  As for the salt tautomers, the illustrations are commonly used in organic chemistry.  EdChem (talk) 13:44, 18 January 2017 (UTC)
 * OK, I misread the tilde (~). A better symbol for approx. is ≈. I could not check your source as there is mo preview available on the web, However, I insist that something is wrong with the pKa value of -1.95. Such a value implies that the compound is effectively a strong acid, much stronger than acetic acid pKa ≈ 4.7 but not quite as strong as hydrochloric acid pKa ≈ -6.3.


 * What may be acceptable to organic chemists is not necessarily right for the general reader of Wikipedia. At the very least I would prefer the notation 0-Na+ but it would be even better to show the acid forms, -OH or -SH as it is they that are involved in the tautomerism.. Petergans (talk) 16:38, 18 January 2017 (UTC)
 * I have changed the image as suggested, and noted it can be taken as an example of resonance in just the anion. The image of the tautomerism in the neutral species is already in the infobox.  I have removed the tilde as well as the source specifies both are above 8.  The google book image of that is available in Australia, you could access it from an Australian IP, or perhaps from the .com link here.  I agree, from a chemical perspective, the pKa of &minus;1.95 is strange, but I was reluctant to ignore it from a reliable source.  I'm willing to post at the Chemistry WikiProject for input, consensus may well be to just leave the 4.6 value that makes sense, or to add a note that a reference indicates a second value.  Also, thanks for the feedback, extra perspectives often help to strengthen an article.  :) EdChem (talk) 22:41, 18 January 2017 (UTC)