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pp.161-167
The kinetics of hydrolysis of cinnamenylisophorone derivatives (rho-H, rho-Br, P-Cl, rho-OCH3) was investigated using ultraviolet spectrophotometry in 20%(v/v) dicxane-H2O at 25℃. A rate equation which can be applied over wide pH range (pH 1.0~13.0) was obtained. In order to investigate the substituent effects on cinnarnenylisophorone derivatives, Hammett constant was plotted. As the result, the rate of hydrolysis of cinnamenylisophorone derivatives was facilitated by electron donating group. Final products of the hydrolysis were benzaldehyde and isophorone, From the measurement of reaction rate constant according to pH changes, substituent effect, and final products, it was found that the hydrolysis of cinnarnenylisophorone derivatives was initiated by the neutral H2O molecule which does not dissociated at below pH 9.0, and in the range of pH 9.0~11.0 this reaction occurs by H2O or hydroxide ion competitively, but proceeded by the hydroxide ion above pH 11.0. On the basis of this kinetic study, the reaction mechanism of the hydrolysis of cinnamenylisophorone derivatives was proposed.
