Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published June 1964 | public
Journal Article

Long-Range Proton Spin—Spin Coupling in Dimethyl Sulfone

Abstract

A wide variety of chemical and spectral data suggest that a sulforic group is capable of interaction with an adjacent unsaturated center ; however, it seems possible that the mode of this interaction may be significantly different from that of conjugation between first-row elements. Moffit's molecular orbital treatment of sulfone groups indicates that two distinct types of conjugation are possible: "direct" conjugation utilizing the filled sulfur-oxygen molecular orbitals for overlap with an adjacent center, and "charge-transfer" conjugation, involving donation of electrons from the adjacent center into utifilled sulfone molecular orbitals having predominantly d-orbital character. It is difficult to distinguish experimentally between these alternatives, but analysis of the e.p.r. spectrum of thioxanthone S,S-dioxide mononegative ion led Vincow to conclude that a charge-transfer mechanism was responsible for the observed conjugation through the sulfone group.

Additional Information

© 1964 American Chemical Society. Received November 26, 1963. Supported in part by the Office of Naval Research and National Science Foundation. Contribution No. 3040.

Additional details

Created:
August 19, 2023
Modified:
October 25, 2023