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Nuclear Magnetic Resonance Spectroscopy. Carbon-carbon Coupling

Weigert, Frank J. and Roberts, John D. (1972) Nuclear Magnetic Resonance Spectroscopy. Carbon-carbon Coupling. Journal of the American Chemical Society, 94 (17). pp. 6021-6025. ISSN 0002-7863. doi:10.1021/ja00772a014.

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One-bond, carbon-carbon coupling constants have been observed for several series of compounds containing ^(13)C in its natural abundance of 1.1% at both sites. The small (10-15 Hz) coupling constants in cyclopropanes show that the carbon-carbon bonds have low s character. Substituent and hybridization effects on the carbon-carbon coupling of aliphatic and alicyclic alcohols, ketones, and five- and six-membered aromatic heterocycles have been observed. Carbon-carbon couplings in methyl derivatives are proportional to carbon-proton coupling in similar bonding situations, with a slope similar to that predicted and observed by Karabatsos for the correlation of carbon-proton and proton-proton couplings. Two- and three-bond carbon-carbon coupling constants are interpreted in terms of the Fermi contact mechanism by correlations with proton-proton and carbon-proton coupling constants in similar bonding situations.

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Additional Information:© 1971 American Chemical Society. Received August 26, 1971. Supported by the National Science Foundation, and the Public Health Service, Research Grant No. GM11072 from the Division of General Medical Sciences. National Science Foundation Predoctoral Fellow. 1965-1968.
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U.S. Public Health Service (USPHS)GM-11072
NSF Predoctoral FellowUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry4320
Issue or Number:17
Record Number:CaltechAUTHORS:20151009-133525573
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Official Citation:Nuclear magnetic resonance spectroscopy. Carbon-carbon coupling in cyclopropane derivatives Frank J. Weigert and John D. Roberts Journal of the American Chemical Society 1967 89 (23), 5962-5963 DOI: 10.1021/ja00999a046
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60953
Deposited By: Ruth Sustaita
Deposited On:15 Oct 2015 23:18
Last Modified:10 Nov 2021 22:42

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