-(Hydroxybenzyl)benzamide Derivatives: Aqueous pH-Dependent Kinetics and Mechanistic Implications for the Aqueous Reactivity of Carbinolamides.

The rate constants for the aqueous reaction, between pH 0 and 14, have been determined for a series of amide substituted -(hydroxybenzyl)benzamide derivatives, in HO, at 25 °C, = 1.0 M (KCl). The -(hydroxybenzyl)benzamide derivatives were found to react via three distinct mechanisms with the kinetically dominant mechanism being dependent on the pH of the reaction solution.