Proton-transfer chemistry of urazoles and related imides, amides, and diacyl hydrazides

…, P Dobrowolski, C Guadalupe-Fasano…

Index: Bausch, M. J.; David, B.; Dobrowolski, P.; Guadalupe-Fasano, C.; Gostowski, R.; et al. Journal of Organic Chemistry, 1991 , vol. 56, # 19 p. 5643 - 5651

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Citation Number: 30

Abstract

Equilibrium acidity constants have been determined for 1, 2, 4-triazolidine-3, 5-dione (urazole), several substituted urazoles, and other related acids, in both dimethyl sulfoxide (DMSO) and aqueous solution. In DMSO, urazole has a pK, of 13.1. In water, urazole has a pK, of 5.8. In general, N-methyl and N-phenyl substituents are found to acidify the urazole moiety, in both DMSO and water. The acidifying effects of these substituents are ...