Spectrochimica Acta Part A: Molecular Spectroscopy

Conformational interactions between a phenyl ring and a side-chain halide substituent: A 1H NMR and molecular mechanics study of some 2-aryl-1-halopropanes

MJ Cook, TJ Howe

Index: Cook, Michael J.; Howe, Trevor J. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 1990 , vol. 46, # 6 p. 957 - 965

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Citation Number: 2

Abstract

Abstract 1 H NMR data are reported for a series of 2-aryl-1-halopropanes. Vicinal coupling constants in the CH 2 CH—fragment show that the rotamer populations about the C C bond are sensitive to para substituents. The ratio of anti: gauche aryl/halide conformers is greatest when the para substituent is the electron-donating ethyl group and least when it is the strongly electron-withdrawing nitro group. This points to a non-steric conformational ...