Solvent effects on alkaline hydrolysis of N-benzylphthalimide in mixed water-acetonitrile and mixed water-N,N-dimethylformamide

2055-2059The nucleophilic second-order rate constant (kOH) for the reaction of OHˉ with Nˉ benzylphthalimide appears to follow a reaction mechanism similar to that for reactions of OHˉ with phthalimide and its N-alkylphthalimides. The rate of hydrolysis reveals an insignificant contribution of water-catalysed cleavage of NBPT compared with its hydroxide ion catalysed reaction. The observed pseudo first-order rate constant, kobs for alkaline hydrolysis of NBPT decreases with increase in the content of organic cosolvents (up to 70%, v/v) in mixed water-CH3CN and water-DMF solvents