Talk:Tautomer

Amines and imines

How are amines and imines tautomers of each other? Enamines and imines makes sense, but not amines and imines, unless I'm missing something. Olin 17:48, 22 March 2006 (UTC)

It's specifically talking about the aminopyridine, not amines in general. The H2N-C=N bond is in fact an enamine...an aza-enamine (the carbon is replaced by the pyridine nitrogen). — Preceding unsigned comment added by 169.237.38.247 (talk) 00:04, 21 November 2006‎ (UTC)

Lactams and lactims

The picture showing "lactam s" and "lactims" is incorrect. The so-called "lactam" is just a primary amide. Lactams are cyclic amides. This portion of the picture is at best unnecessary. —Preceding unsigned comment added by 142.157.48.16 (talk) 20:18, 12 July 2010 (UTC)

Seems resolved now. Both lactam-lactim diagrams are cyclic. DMacks (talk) 02:50, 16 June 2017 (UTC)

Organic only?

Should the definition of tautomer refer (seemingly solely) to organic compounds? Googling show some non-Wikipedia source agree; others do not. Indeed, "tautomer" is used in Wikipedia in relation to sulfamic acid.NickSharp (talk) 20:27, 22 June 2013 (UTC)

Common man

Give some examples for the common man. E.g., "the smell of rotten fruit is an example of a tautomer" Jidanni (talk) 10:50, 8 April 2010 (UTC)

Uses?

Could someone give examples of uses for this principle? Commercial processes and products? Potential new applications?

Karl gregory jones (talk) 12:56, 16 August 2015 (UTC)

Explain it!

You can't 'explain' tautomers as being 'constitutional isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization'; and not explain what tautomerization is... 97.84.122.189 (talk) 03:23, 30 December 2015 (UTC)

Request diagram for the nitroso - oxime pair

A diagram for the nitroso - oxime pair should make it clearer. - Rod57 (talk) 05:34, 29 March 2016 (UTC)

Energy levels

Can anyone say what typical energy difference between the tautomers of a pair ? Can we have a formula for the equilibrium ratio ? How fast (formula ?) do the tautomers interconvert ? - Rod57 (talk) 05:39, 29 March 2016 (UTC)

I suspect the answer to these questions is that there are no typical values, because there are very wide variations (of energy differences, equilibrium ratios and interconversion rates) between different pairs of tautomers. Dirac66 (talk) 02:06, 16 June 2017 (UTC)

Valence tautomer examples

The article now claims that azide (N₃^-) and tetrazole (CH₂N₄) are valence tautomers, which is clearly wrong as the definition of tautomers states that they are isomers. The revision history shows that this information was added on 1 July 2006 by an editor who has been inactive for 10+ years with no talk page, so it is impossible to contact him/her. So I think it would be best to just delete this incorrect example.

The "azide" in azide–tetrazole is an organoazide structure, not the azide anion itself. In that light, it would be an iminomethylazide, and doi:10.1021/jo902342z gives an example. Likewise, we could have vinylazide–triazole as noted in doi:10.1021/acs.chemrev.6b00738. DMacks (talk) 02:58, 16 June 2017 (UTC)

As for the second example, münchnone is C₃NO₂H₃) as per the structure of the linked article. The formula of acylaminoketene depends on what is meant by acyl. If acyl is formyl then we have HCO-NH-CH=C=O which does have the same formula as munchnone, so perhaps the article should say formylaminoketene.

A correct example is given by IUPAC at valence tautomerization. I would add this example except that I am not certain of the correct names of the molecules shown. Perhaps epoxycyclohexadiene and oxacycloheptatriene? Dirac66 (talk) 02:06, 16 June 2017 (UTC)

That exact example is already in Oxepin. DMacks (talk) 02:59, 16 June 2017 (UTC)

Thanks. I have now placed the oxepin - benzene oxide pair first since they are the simplest structures and also the Gold Book example. And I have included your source for azide-tetrazole. Dirac66 (talk) 01:49, 17 June 2017 (UTC)