Nucleophilic character of acyl radicals. Substituent effects on the homolytic acylation of protonated heteroaromatic bases
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1477-1481
- https://doi.org/10.1039/p29720001477
Abstract
The relative rates of the homolytic acylation of protonated 2- and 4-substituted quinolines with acetyl and benzoyl radicals are reported. Orientation of products and reactivity show clear-cut nucleophilic character for the acyl radicals. The relative rates have not been correlated with the Hammett σm constants because of enhanced conjugation of the electron-releasing substituents. A much smaller effect is observed for substituted benzoyl radicals; in this case a Hammett correlation gives ρ=–0·49.Keywords
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