Acid dissociation constants of phenols and reaction mechanism for the reactions of substituted phenyl benzoates with phenoxide anions in absolute ethanol

Abstract

Acid dissociation constants of 10 substituted phenols have been measured by a kinetic method together with second-order rate constants for the reactions of aryl benzoates (X-C6H4CO-OC6H4-Y) with Z-substituted phenoxide (Z-C6H4O-) and EtO- in absolute ethanol at 25.0 ± 0.1°C. The kinetic results support a stepwise mechanism for the present acyl-transfer reaction.