A comparison of the effects of phenyl, pyridyl, and pyridinio substituents upon keto–enol tautomerisation and enol ionisation equilibria of acetophenone shows that polar effects upon bond hybridisation and resonance interaction with ‘neutral’ double bonds are important influences upon enol stability.
A. R. E. Carey, S. Al-Quatami, R. A. M. O'Ferrall and B. A. Murray, J. Chem. Soc., Chem. Commun., 1988, 1097 DOI: 10.1039/C39880001097
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