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Electronic and steric effects in the SNAr substitution reactions of substituted anilines with 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether in acetonitrile.

Crampton, M. R. (2006) 'Electronic and steric effects in the SNAr substitution reactions of substituted anilines with 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether in acetonitrile.', Journal of physical organic chemistry., 19 (1). pp. 75-80.

Abstract

Rate measurements are reported for the reactions of 12 ring-substituted anilines with 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether (1) in acetonitrile. Formation of the products, the correspondingly substituted 2,4,6-trinitrodiphenylamines, occurs without the observation of intermediates in detectable amounts by both base-catalysed and uncatalysed pathways and Hammett value were determined for these processes. The results show that although substituents at the 3- or 4-positions of the anilines have only small steric effects, alkyl substituents at the 2-position may result in considerable reductions in reactivity. These effects are more pronounced for the base-catalysed pathway and in 2,6-dimethylaniline the uncatalysed pathway takes all the reaction flux. In the case of the 2-fluoro substituent the electronic effect, strong inductive electron withdrawal, is dominant over steric effects.

Item Type:Article
Keywords:SNAr substitution reactions, Anilines, 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether, Electronic effects, Steric effects.
Full text:Full text not available from this repository.
Publisher Web site:http://dx.doi.org/10.1002/poc.997
Record Created:26 Apr 2007
Last Modified:08 Apr 2009 16:30

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