Michael R. Crampton
Electronic and steric effects in the SNAr substitution reactions of substituted anilines with 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether in acetonitrile
Crampton, Michael R.; Emokpae, Thomas A.; Isanbor, Chukwuemeka
Authors
Thomas A. Emokpae
Chukwuemeka Isanbor
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.
Citation
Crampton, M. R., Emokpae, T. A., & Isanbor, C. (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), 75-80. https://doi.org/10.1002/poc.997
Journal Article Type | Article |
---|---|
Acceptance Date | Sep 7, 2005 |
Online Publication Date | Oct 28, 2005 |
Publication Date | Jan 1, 2006 |
Deposit Date | Apr 26, 2007 |
Journal | Journal of Physical Organic Chemistry |
Print ISSN | 0894-3230 |
Electronic ISSN | 1099-1395 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 19 |
Issue | 1 |
Pages | 75-80 |
DOI | https://doi.org/10.1002/poc.997 |
Keywords | SNAr substitution reactions, Anilines, 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether, Electronic effects, Steric effects. |
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