Use of Substituent Effects on Isotope Effects to Distinguish between Proton and Hydride Transfers. Part I. Mechanism of Oxidation of Alcohols by Bromine in Water1-3

CG Swain, RA Wiles, RFW Bader

Index: Swain,C.G. et al. Journal of the American Chemical Society, 1961 , vol. 83, p. 1945 - 1950

Full Text: HTML

Citation Number: 62

Abstract

Differences between proton and hydride transfers are discussed. Theoretical reasons are given for expecting kH/kD isotope effects to increase markedly on introduction of electron- attracting substituents for proton transfers, but to be much less sensitive to substituents for hydride transfers. Therefore it is applied as a tool for distinguishing between proton and hydride transfers in the oxidation of 0.01-. 1 M 2-propanol by 0.001-0.008 This reaction is ...