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Nuclear Magnetic Resonance Spectroscopy. The Effect of Structure on Magnetic Nonequivalence Due to Molecular Asymmetry

Whitesides, George M. and Holtz, David and Roberts, John D. (1964) Nuclear Magnetic Resonance Spectroscopy. The Effect of Structure on Magnetic Nonequivalence Due to Molecular Asymmetry. Journal of the American Chemical Society, 86 (13). pp. 2628-2634. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151016-112436493

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Abstract

The difference in chemical shift between the methylene protons of a number of compounds related structurally to 1-phenylethyl benzyl ether has been measured. Correlations between structural features of these compounds and the magnitude of the magnetic nonequivalence induced by the center of molecular asymmetry provide a basis for qualitative identification of the most important factors contributing to the chemical-shift difference. Although it is clear that no single factor Completely determines the magnitude of the methylene proton nonequivalence in these ethers, it is suggested that the proximity of the asymmetric center to the benzyl group results in a preferred conformation of the phenyl ring with respect to the methylene protons, and that the principal contribution to the nonequivalence originates in the magnetic anisotropy of the phenyl group.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01067a022DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01067a022PublisherArticle
ORCID:
AuthorORCID
Whitesides, George M.0000-0001-9451-2442
Additional Information:© 1964 American Chemical Society. Received February 20, 1964. Supported in part by the Office of Naval Research and the Undergraduate Research Participation Program of the National Science Foundation.
Funders:
Funding AgencyGrant Number
Office of Naval Research (ONR)UNSPECIFIED
NSF Undergraduate Research ProgramUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry3072
Issue or Number:13
Record Number:CaltechAUTHORS:20151016-112436493
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151016-112436493
Official Citation:Nuclear Magnetic Resonance Spectroscopy. The Effect of Structure on Magnetic Nonequivalence Due to Molecular Asymmetry George M. Whitesides, David. Holtz, and John D. Roberts Journal of the American Chemical Society 1964 86 (13), 2628-2634 DOI: 10.1021/ja01067a022
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61202
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 Oct 2015 21:29
Last Modified:09 Mar 2020 13:19

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