Aspects of tautomerism. Part V. Solvent, substituent, and steric effects on the ring–chain tautomerism of o-benzoylbenzamides

Ring-chain tautomeric equilibria of o-benzoylbenzamides in 95% ethanol, chloroform, dioxan, and acetonitrile have been estimated using u.v. spectroscopy. Unlike the case of acids, solvent polarity has only a small effect. In ethanol the cyclic form is favoured. Electron-withdrawing groups in the amide-bearing ring disfavour the cyclic form. Substitution of methyl, ethyl, and phenyl groups on the nitrogen atom of the amide function results in increase of the proportion of the cyclic form in the first two cases and decrease in the last.