HYDROLYSIS OF N-SALICYLIDENE-2-METHOXYETHYLAMINE. INTRAMOLECULAR GENERAL BASE CATALYSIS AND SPECIFIC EFFECTS OF BORIC ACID.

Article abstract of DOI:10.1246/bcsj.57.2502

Hydrolysis of N-salicylidene-2-methoxyethylamine is kinetically investigated at 30 degree C. Intramolecular general base catalysis by the o-O** minus substituent takes place in the neutral pH region. Nucleophilic catalysis by morpholine was also found to be operative. Added boric acid accelerates the hydrolysis above pH 5. 5 while it decelerates the hydrolysis below pH 5. 5. The hydrolysis rate as the function of the boric acid concentration follows a saturation curve in harmony with a reaction sequence involving a rapid equilibrium formation of a borate-substrate complex followed by its breakdown. The morpholine catalysis is inhibited by boric acid in accord with the slow reaction of morpholine with the complex.