Journal of the American Chemical Society

Nonadditivity of secondary deuterium isotope effects on basicity of trimethylamine

CL Perrin, Y Dong

Index: Perrin, Charles L.; Dong, Yanmei Journal of the American Chemical Society, 2008 , vol. 130, # 33 p. 11143 - 11148

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Citation Number: 11

Abstract

Secondary deuterium isotope effects (IEs) on basicities of isotopologues of trimethylamine have been accurately measured by an NMR titration method applicable to a mixture. Deuteration definitely increases the basicity, by∼ 0.021 in the Δp K per D. The IE is attributed to the lowering of the CH stretching frequency and zero-point energy by delocalization of the nitrogen lone pair into the C− H antibonding orbital. Because this ...