Carbinol Derivatives of N-(α-Hydroxybenzyl)benzamide: Acid and Base-Dependent Kinetics in Water and the Mechanistic Implications for Carbinolamide Reactivity

摘要

The kinetics of the aqueous reaction, between pH values of 0-4 & 7-14, have been determined for a series of carbinol substituted N-(α-hydroxybenzyl)benzamide derivatives (5), in H2O, at 25°C, I=1.0 M (KCl). The carbinol derivatives of 5 were found to react via two mechanisms. Between pH values of 0 to 4, an acid-catalyzed mechanism was found and under neutral/ basic conditions the carbinolamides reacted by a specific-base catalyzed mechanism (E1cB-like mechanism). No evidence for mechanistic variation of the acid and base-catalyzed reactions based upon the carbinol substituent was found.