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KMID : 1059519890330010127
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Journal of the Korean Chemical Society
1989 Volume.33 No. 1 p.127 ~ p.134
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Kinetic Studies on the Nucleophilic Addition of 3-Mercaptopropionic Acid to β,β-Diethoxycarbonylstyrene Derivatives
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Kim Tae-Rin
Choi Yun-Chung
Chung Myung-Sook
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Abstract
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The rate constants of the nucleophilic addition reaction of 3-mercaptopropionic acid to the β,β-diethoxycarbonylstryene derivatives (H, p-OCH3, 3,4,5-(OCH3)3, 3,4-methylenedioxy) were determined by ultraviolet spectrophotometry, and rate equation which could be applied over a wide pH range was obtained. On the basis of pH-rate profile and the presence of general base catalysis, a plausible mechanism of this addition reaction was propound:Below pH 6.0 the reaction was initiated by the addition of neutral 3-mercaptopropionic acid molecule, and in the range of pH 6.0∼8.0, a neutral 3-mercaptopropionic acid molecule and a sulfide anion competitively attacked to the double bond. Above pH 8.0, the reaction proceeded through the addition of a sulfide anion.
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