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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The SN Mechanism in aromatic compounds. 25. Substituent effects of multiple-bond nitrogen.

J Miller and AJ Parker

Australian Journal of Chemistry 11(3) 302 - 308
Published: 1958

Abstract

The substituent effects in aromatic nucleophilic substitution of groups attached to the benzene ring by a multiple-bond nitrogen atom are considered. Attachment is para to a replaceable halogen atom, and generally as a 4-substituent to l-chloro-2-nitrobenzene. Comparisons with some other groups are shown. Reasons are given for the greater T effect of a triple than of a double bond. Hammett substituent constants (σ*) are computed. Those for the nitroso and diazonium groups .are the largest so far obtained for electrically neutral and cationic groups respectively. The activating power of four of the nitrogen groups in electrophilic as well as nucleophilic substitution is discussed briefly.

https://doi.org/10.1071/CH9580302

© CSIRO 1958

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