Roberts, John D. and Christl, Manfred and Reich, Hans J. (1971) Nuclear Magnetic Resonance Spectroscopy. Carbon-13 Chemical Shifts of Methycyclopentanes, Cyclopentanols, and Cyclopentyl Acetates. Journal of the American Chemical Society, 93 (14). pp. 3463-3468. ISSN 0002-7863. doi:10.1021/ja00743a028. https://resolver.caltech.edu/CaltechAUTHORS:20151012-133438143
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Abstract
The ^(13)C chemical shifts of the title compounds have been determined by high-resolution nmr spectroscopy with the aid of proton decoupling. Substituent effects have been computed and compared to those obtained for some corresponding cyclohexane compounds, with the hope of providing information about steric interactions and conformations of cyclopentane derivatives. Rather large downfield ɑ (up to ~24 ppm) and β (up to ~7 ppm) shifts were observed on dissolution of up to 0.5 M europium tris(dipiva1omethane) in cyclopentanols. The cis- and trans-3-methyl- and 1,3-dimethylcyclopentanols showed somewhat different chelate shifts which could be used to help assign the stereochemical configuration of these substances. The ^(13)C chemical-shift changes produced by chain branching in some aliphatic acetates and ethers are compared and rationalized.
| Item Type: | Article | |||||||||
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| Additional Information: | © 1971 American Chemical Society. Received October 7, 1970. Supported by the National Science Foundation. Max Kade Foundation, Inc. Fellow, 1970-1971; National Research Council of Canada Postdoctoral Research Fellow. | |||||||||
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| Issue or Number: | 14 | |||||||||
| DOI: | 10.1021/ja00743a028 | |||||||||
| Record Number: | CaltechAUTHORS:20151012-133438143 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151012-133438143 | |||||||||
| Official Citation: | Nuclear magnetic resonance spectroscopy. Carbon-13 chemical shifts of methycyclopentanes, cyclopentanols, and cyclopentyl acetates John D. Roberts, Manfred Christl, and Hans J. Reich Journal of the American Chemical Society 1971 93 (14), 3463-3468 DOI: 10.1021/ja00743a028 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 60991 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 15 Oct 2015 04:09 | |||||||||
| Last Modified: | 10 Nov 2021 22:42 |
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