Nucleophilic displacement in polyhalogenoaromatic compounds. Part 1. Kinetics of reaction of polychlorofluorobenzene derivatives
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 13,p. 1541-1545
- https://doi.org/10.1039/p29760001541
Abstract
The rate; of displacement of fluorine from some polychloropolyfluorobenzene derivatives by sodium methoxide in methanol have been studied. The second-order rate constants show a dependence upon halogen substituent effects similar to that found in aromatic nucleophilic displacement reactions with other activating groups. The mechanisms by which halogen substituents activate benzene systems to such attack are discussed: only two, classical electronic interactions are needed. A simple numerical method is described which enables the prediction of rates and orientations of displacement, and of 19F n.m.r. shifts, in polyhalogenobenzene derivatives.Keywords
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