Stereochemistry of β-deuterium isotope effects on amine basicity

…, J Kuperman, J Liberman, M Erdélyi

Index: Perrin, Charles L.; Ohta, Brian K.; Kuperman, Joshua; Liberman, Jordan; Erdelyi, Mate Journal of the American Chemical Society, 2005 , vol. 127, # 26 p. 9641 - 9647

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Citation Number: 40

Abstract

Secondary β-deuterium isotope effects on amine basicities are measured using a remarkably precise NMR titration method. Deuteration is found to increase the basicity of methylamine, dimethylamine, benzylamine, N, N-dimethylaniline, 2-methyl-2- azanorbornane, and pyrrolizidine. The increase in dimethylamine arises entirely from enthalpy, contrary to a previous report. The method permits a determination of ...