Non-dissociative proton transfer in 2-pyridone–2-hydroxypyridine. An ab initio molecular orbital study

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Abstract
The lactim–lactam tautomerism of 2-pyridone via non-dissociative proton-transfer mechanisms has been investigated using ab initio MO methods. Stationary points (minima and saddle points) on the potential energy surfaces for proton transfer by three classes of such mechanisms have been obtained: (i) an intramolecular mechanism, (ii) tautomeric interconversion within a self-associated dimer, and (iii) a mechanism involving one or two water molecules as a bifunctional catalyst. The latter two mechanisms were found to be more energetically favourable than the first. The role of bulk solvent on the energetics of proton transfer by these mechanisms has been investigated.

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