Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies of the Solvent Effects on the Chemical Shifts in NMR Spectroscopy. III. The Benzene Solutions of Cyclic Ketones and Lactones
Yukihiko IchikawaTaku Matsuo
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1967 Volume 40 Issue 9 Pages 2030-2034

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Abstract

The high-field shifts of the proton signals of cyclic ketones and lactones in the benzene solutions have been investigated. The solvent effects on the chemical shifts for the β-methylene protons of these compounds are always larger than those for the α-methylene protons. The data may be explained by the use of a model in which benzene molecules are assumed to cluster around the carbonyl group of the solute. The affinity between the solute and the solvent molecules has been mainly ascribed to the fact that both the permanent electric dipole moment and the instantaneous dipole moment of the carbonyl (or carboxyl) group induce electric dipole moments in the near-by benzene molecules. The configuration and the number of the solvent molecules clustering around the solute have been suggested to be determined by the geometrical restriction around the carbonyl group.

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