Journal of the American Chemical Society

Effects of structural changes on acidities and homolytic bond dissociation energies of the hydrogen-nitrogen bonds in amidines, carboxamides, and thiocarboxamides

FG Bordwell, GZ Ji

Index: Bordwell, Frederick G.; Ji, Guo-Zhen Journal of the American Chemical Society, 1991 , vol. 113, # 22 p. 8398 - 8401

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Citation Number: 114

Abstract

Abstract: The equilibrium acidities in DMSO have been measured for acetamidine, benzamidine, A',“-diphenylbenzamidine, NJV-diethylbenzamidine, diphenylmethanimine, guanidine, N,” diphenylguanidine, Nfl'diphenylurea, and” diphen ylthiourea. Combination of the resulting pKHA values for these weak acids with the oxidation potentials of their conjugate bases gave estimates of their homolytic bond dissociation energies (BDEs). ...