The Journal of Organic Chemistry

Mechanism of the racemization of amino acids. Kinetics of racemization of arylglycines

GG Smith, T Sivakua

Index: Smith, Grant Gill; Sivakua, Thipamon Journal of Organic Chemistry, 1983 , vol. 48, # 5 p. 627 - 634

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Citation Number: 76

Abstract

In a study of the rates of racemization of substituted arylglycines [ArCH (NH&OOH] at pH 10, the Hammett u value was found to be surprisingly low, 1.15, suggesting a concerted reaction or charge stabilization in a manner other than by the substituent. The rate of methine hydrogen exchange was, however, the same as the rate of racemization, which argues against a concerted reaction mechanism. A pH profile study demonstrated that the most ...