Equilibrium acidities and homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in N-substituted trimethylammonium and pyridinium cations

XM Zhang, FG Bordwell, M Van Der Puy…

Index: Zhang, Xian-Man; Bordwell, Frederick G.; Puy, Michael Van Der; Fried, Herbert E. Journal of Organic Chemistry, 1993 , vol. 58, # 11 p. 3060 - 3066

Full Text: HTML

Citation Number: 56

Abstract

Equilibrium acidities (pKms) of the cations in sixteen N-substituted trimethylammonium salts, one N-phenacylquinuclidinium salt, eight N-substituted pyridinium salts, and N- (ethoxycarbonyl)-isoquinolinium bromide, together with the oxidation potentials of their conjugate bases, have been determined in dimethyl sulfoxide (DMSO) solution. The acidifying effects of the a-trimethylammonium groups (a-Me3N+) and the a-pyridinium ...