Weigert, Frank J. and Roberts, John D. (1971) ^(13)C nuclear magnetic resonance spectroscopy. Determination of carbon-fluorine couplings. Journal of the American Chemical Society, 93 (10). pp. 2361-2369. ISSN 0002-7863. doi:10.1021/ja00739a001. https://resolver.caltech.edu/CaltechAUTHORS:20151012-133439259
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Abstract
One-, two-, three-, and four-bond carbon-fluorine coupling constants have been observed for a series of substituted fluorobenzenes. The one-bond coupling constants in the para derivatives are proportional to the fluorine chemical shifts, but a similar correlation shows considerable scatter for the meta derivatives and is invalid for the ortho derivatives. The carbon-fluorine coupling constants in fluorobenzene are JCF= -245.3, JCCF= +21.0, JCCGF) = + 7.7, and Jccccr = +3.3 Hz. Consistent explanations of the substituent effects on the long-range coupling constants have not been found. All the carbons in l-fluoronaphthalene are coupled to the fluorine with magnitudes of 0.6 to 250 Hz. The fluorine in 2-fluoronaphthalene is coupled to only six carbons, presumably those in the same ring as the fluorine. The carbon-fluorine coupling constants in n-hexyl fluoride are JCF = - 166.6, JCCF = +19.9, and JcccF= 5.25 Hz. The one-bond carbon-fluorine couplings in cyclic geminal difluorides vary with ring size. The fluorine substituent effect on the chemical shifts of carbons y to the fluorine is discussed in terms of proposed steric perturbation mechanisms.
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| Additional Information: | © 1971 American Chemical Society. Received June 18, 1970. Supported in part by the National Science Foundation. Some of the data in this paper were reported in preliminary paper: F. J. Weigert and J. D. Roberts,J. Amer. Chem. Soc., 91,4940 (1969). (2) National Science Foundation Predoctoral Fellow, 1965-1968. | |||||||||
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| Issue or Number: | 10 | |||||||||
| DOI: | 10.1021/ja00739a001 | |||||||||
| Record Number: | CaltechAUTHORS:20151012-133439259 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151012-133439259 | |||||||||
| Official Citation: | Carbon-13 nuclear magnetic resonance spectroscopy. Determination of carbon-fluorine couplings John D. Roberts and Frank J. Weigert Journal of the American Chemical Society 1971 93 (10), 2361-2369 DOI: 10.1021/ja00739a001 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 60995 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 13 Oct 2015 21:24 | |||||||||
| Last Modified: | 10 Nov 2021 22:42 |
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