Hiroaki Nagamatsu, T. Okuyama, T. Fueno
Sep 1, 1984
Citations
0
Influential Citations
9
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Hydrolysis of N-salicylidene-2-methoxyethylamine is kinetically investigated at 30 °C. Intramolecular general base catalysis by the o-O− 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. The water reaction of the complex is considered to involve a rearrangement of the complex and an intramolecular transfer of the boron-coordinated hydroxide ion to the iminium carbon.