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Long-Range Proton Spin—Spin Coupling in Dimethyl Sulfone

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. 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/j100788a512DOIArticle
http://pubs.acs.org/doi/abs/10.1021/j100788a512PublisherArticle
ORCID:
AuthorORCID
Whitesides, George M.0000-0001-9451-2442
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.
Funders:
Funding AgencyGrant Number
Office of Naval Research (ONR)UNSPECIFIED
NSFUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry3040
Issue or Number:6
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:09 Mar 2020 13:19

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