Journal of the American Chemical Society

Position-specific secondary deuterium isotope effects on basicity of pyridine

CL Perrin, P Karri

Index: Perrin, Charles L.; Karri, Phaneendrasai Journal of the American Chemical Society, 2010 , vol. 132, # 34 p. 12145 - 12149

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Citation Number: 18

Abstract

Secondary isotope effects (IEs) on basicities of various deuterated pyridine isotopologues and of 2, 6-lutidine-2, 6-(CD3) 2 have been accurately measured in aqueous solution by an NMR titration method applicable to a mixture. Deuteration at any position of pyridine increases the basicity, but the IE per deuterium is largest for substitution at the 3-position and smallest for the 2-position, which is closest to the site of N-protonation, smaller even ...