Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with α, β-unsaturated compounds1, 2

M Friedman, JF Cavins, JS Wall

Index: Friedman,M. et al. Journal of the American Chemical Society, 1965 , vol. 87, p. 3672 - 3682

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Citation Number: 294

Abstract

Factors were investigated which govern nucleophilic reactivities of functional groups in aminothiols, thiols, and other model compounds with &-unsaturated compounds such as acrylonitrile. Rates as a function of p H correlate with theoretical rate equations and indicate that mercaptide ions and nonprotonated amino groups participate in the rate-determining step. Possible reaction pathways of aminothiols are considered in terms of the two ...