Kinetics and Mechanism of Alkaline Hydrolysis of N-(o-Aminophenyl)Phthalimide in the Presence and Absence of Cationic Micelles and Sodium Salts of Aliphatic Acids

Abstract

Pseudo first-order rate constants, k obs , for the alkaline hydrolysis of N-(o-aminophenyl) phthalimide, obtained at constant [CTABr]T (total concentration of cetyltrimethylammonium bromide) and varying concentrations of inert salt MX (MX = sodium formate, sodium acetate, sodium propanoate, sodium butyrate, sodium valerate and sodium hexanoate) follow the relationship: k obs = ( k 0 + θ K X / S [ MX ] ) ( 1 + K X / S [ MX ] ) , where θ and KX/S are empirical constants and S = HO-. The values of KX/S for each aliphatic acid decrease with an increase in [CTABr]T. This relationship gives an empirical constant whose magnitude is the measure of the ability of an ion, X-, to expel another counterion S-, from the cationic micellar surface to the bulk aqueous phase. The values of the empirical constant, KX/S, are used to derive the ion exchange constant, KBrX.