Whitesides, George M. and Roberts, John D. (1964) Long-Range Proton Spin—Spin Coupling in Dimethyl Sulfone. Journal of Physical Chemistry, 68 (6). pp. 1583-1584. ISSN 0022-3654. doi:10.1021/j100788a512. https://resolver.caltech.edu/CaltechAUTHORS:20151016-143423827
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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.
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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. | |||||||||
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Issue or Number: | 6 | |||||||||
DOI: | 10.1021/j100788a512 | |||||||||
Record Number: | CaltechAUTHORS:20151016-143423827 | |||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151016-143423827 | |||||||||
Official Citation: | Long-Range Proton Spin—Spin Coupling in Dimethyl Sulfone George M. Whitesides and John D. Roberts The Journal of Physical Chemistry 1964 68 (6), 1583-1584 DOI: 10.1021/j100788a512 | |||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
ID Code: | 61219 | |||||||||
Collection: | CaltechAUTHORS | |||||||||
Deposited By: | Ruth Sustaita | |||||||||
Deposited On: | 16 Oct 2015 22:34 | |||||||||
Last Modified: | 10 Nov 2021 22:45 |
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