Petterson, Krag A. and Stein, Robin S. and Drake, Michael D. and Roberts, John D. (2005) An NMR investigation of the importance of intramolecular hydrogen bonding in determining the conformational equilibrium of ethylene glycol in solution. Magnetic Resonance in Chemistry, 43 (3). pp. 225-230. ISSN 0749-1581. doi:10.1002/mrc.1512. https://resolver.caltech.edu/CaltechAUTHORS:20150930-125953201
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Abstract
Although conformational analysis by NMR of ethylene glycol indicates generally strong preferences for the gauche conformation in solvents ranging from water to chloroform, the bulk of the NMR evidence indicates that intramolecular hydrogen bonding between the hydroxyl groups is unlikely to be a significant factor in determining that preference, except possibly in fairly non-polar solvents. The ‘gauche effect’ is clearly very important, especially in aqueous solution.
| Item Type: | Article | ||||||||||||||||
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| Additional Information: | © 2005 John Wiley & Sons, Ltd. Received 27 May 2004; Revised 23 September 2004; Accepted 24 September 2004. Article first published online: 1 Feb 2005. This work was supported by the donors of the Petroleum Research Fund, administered by the American Chemical Society, the National Science Foundation (CHE-0104273), the Caltech Summer Undergraduate Research Fellowship Program (SURF), E. I. DuPont Company, Dr and Mrs Chester M. McCloskey, the Camille and Henry Dreyfus Foundation (SI-04-015) and Merck and Company. | ||||||||||||||||
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| Subject Keywords: | NMR; ^1H NMR; ^(13)C NMR; conformational analysis; intramolecular hydrogen bonding; solvent effects; gauche effect; glycols; ethylene glycol | ||||||||||||||||
| Issue or Number: | 3 | ||||||||||||||||
| DOI: | 10.1002/mrc.1512 | ||||||||||||||||
| Record Number: | CaltechAUTHORS:20150930-125953201 | ||||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20150930-125953201 | ||||||||||||||||
| Official Citation: | Petterson, K. A., Stein, R. S., Drake, M. D. and Roberts, J. D. (2005), An NMR investigation of the importance of intramolecular hydrogen bonding in determining the conformational equilibrium of ethylene glycol in solution. Magn. Reson. Chem., 43: 225–230. doi: 10.1002/mrc.1512 | ||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||
| ID Code: | 60617 | ||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||
| Deposited By: | Ruth Sustaita | ||||||||||||||||
| Deposited On: | 30 Sep 2015 21:14 | ||||||||||||||||
| Last Modified: | 10 Nov 2021 22:36 |
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