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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Electronic effects of halogen-substituted methyl groups

CW Fong

Australian Journal of Chemistry 33(6) 1291 - 1300
Published: 1980

Abstract

The electronic effects of the halogen-substituted methyl groups, CHnX3-n, where X is F, Cl, Br or I, have been examined by 13C n.m.r, spectroscopy in a series of α-halogen-substituted toluenes. The substituent chemical shifts of all carbon atoms, as well as the σI and σR0 substituent parameters derived from a dual substituent parameter (DSP) analysis, are examined in terms of hyperconjugative and π-inductive substituent effects. Bulky CHnX3-n substituents cause molecular deformations of the benzene ring, consequently invalidating the derivation of substituent parameters from a DSP analysis.

https://doi.org/10.1071/CH9801291

© CSIRO 1980

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