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

Article abstract of DOI:10.1016/S0040-4020(97)00227-5

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.