Bulletin of the Chemical Society of Japan p. 500 - 505 (1984)
Update date:2022-08-29
Topics:
Matsuda
Nagamatsu
Okuyama
Fueno
Effects of boric acid on the rate of hydrolysis of a Schiff base derived from alpha -hydroxyisobutyrophenone and 2-methoxyethylamine were examined in the pH range 4. 2-10. 4 at 30 degree C. The rate increased above pH 7 but decreased below pH 7 with increasing borate concentration following a saturation curve. This is consistent with a reaction sequence involving a preequilibrium formation of a borate-substrate complex followed by its rate-determining decay to the hydrolysis products. The formation constant of the complex showed a bell-shaped change with pH but the rate constant for the complex decay was constant above pH 7, a small change being observed at lower pH. A mechanism involving an intramolecular transfer of the boron-coordinated hydroxide ion to the imine carbon within the complex is presented.
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