Improved methods for the N-nitration of amides

…, M Aragones, J Garcia, J Vilarrasa

Index: Romea, Pedro; Aragones, Montse; Garcia, Jordi; Vilarrasa, Jaume Journal of Organic Chemistry, 1991 , vol. 56, # 25 p. 7038 - 7042

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Citation Number: 18

Abstract

Conclusions Since the rates of nitrogen inversion in hydroxylamines and their conjugate bases are the same, we conclude that the effect of increased lone-pair repulsion of-0-is equal to the u-inductive effect of its reduced electronegativity. These two effects happen to cancel nearly exactly, so that there is no net effect. This cancellation represents a CHE90- 25113. challenge to MO calculations. It is no surprise that these two effects had not ...