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Nuclear Magnetic Resonance Spectroscopy. Conformational Properties of Cyclobutanes. Variation of Geminal Fluorine—Fluorine Chemical-Shift Differences with Temperature

Lambert, Joseph B. and Roberts, John D. (1965) Nuclear Magnetic Resonance Spectroscopy. Conformational Properties of Cyclobutanes. Variation of Geminal Fluorine—Fluorine Chemical-Shift Differences with Temperature. Journal of the American Chemical Society, 87 (17). pp. 3884-3890. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151015-104929684

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Abstract

The temperature dependence of the geminal fluorine-fluorine chemical-shift differences in a variety of unsymmetrically substituted cyclobutanes is interpreted in terms of a classical equilibrium between axial and equatorial conformations. With the assumption that the conformations have the same entropy, free-energy differences between the conformers are calculated and discussed. The axial conformer in monosubstituted cyclobutanes may be nearly planar. The absence of temperature effects in the spectra of a cyclobutene and a cyclobutanone indicates that these systems are statically planar. The angle of puckering of I,1-difluoro-3-phenylcyclobutane is calculated by the dipole moment method to be about 27º.


Item Type:Article
Related URLs:
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http://dx.doi.org/10.1021/ja01095a016DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01095a016PublisherArticle
Additional Information:© 1965 American Chemical Society. Received May 12, 1965. Supported in part by the Office of Naval Research and the National Science Foundation. National Science Foundation Predoctoral Fellow, 1962-1965.
Funders:
Funding AgencyGrant Number
Office of Naval Research (ONR)UNSPECIFIED
NSFUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry3229
Record Number:CaltechAUTHORS:20151015-104929684
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151015-104929684
Official Citation:Nuclear Magnetic Resonance Spectroscopy. Conformational Properties of Cyclobutanes. Variation of Geminal Fluorine—Fluorine Chemical-Shift Differences with Temperature Joseph B. Lambert and John D. Roberts Journal of the American Chemical Society 1965 87 (17), 3884-3890 DOI: 10.1021/ja01095a016
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61169
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 Oct 2015 17:43
Last Modified:16 Oct 2015 17:43

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