Substituent effects on benzylic radical hydrogen hyperfine coupling constants. Part 4. The effect of branching of the alkyl substituent

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DOIResolve DOI: http://doi.org/10.1139/v85-394
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TypeArticle
Journal titleCanadian Journal of Chemistry
Volume63
Issue9
Pages2378–2383
AbstractThe effects of substituents in the meta and para positions of the benzyl radical on the ?-hydrogen hyperfine coupling constants (hfc's) are discussed. The electron spin resonance (esr) spectra of the para-methyl, ethyl, isopropyl, and tert-butyl substituted benzyl and cumyl radicals are analysed. Hyperconjugation involving the C—C bond is 40–60% as effective as C—H hyperconjugation for delocalizing spin density. This conclusion is supported by INDO molecular orbital calculations. Similar analysis of the 13Cmr spectra of the para-alkyl substituted cumyl carbocations provides evidence that C—C hyperconjugation is 75–90% as effective as C—H hyperconjugation for delocalizing charge density.
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LanguageEnglish
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NPARC number12338036
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Record identifier8b47f189-b6b1-45e8-b76e-dfd1f544da22
Record created2009-09-10
Record modified2016-05-09
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