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An NMR investigation of the importance of intramolecular hydrogen bonding in determining the conformational equilibrium of ethylene glycol in solution

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. http://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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/mrc.1512DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/mrc.1512/abstractPublisherArticle
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.
Funders:
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
NSFCHE-0104273
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
E. I. DuPont CompanyUNSPECIFIED
Dr and Mrs Chester M. McCloskeyUNSPECIFIED
Camille and Henry Dreyfus FoundationSI-04-015
Merck and CompanyUNSPECIFIED
Subject Keywords:NMR; ^1H NMR; ^(13)C NMR; conformational analysis; intramolecular hydrogen bonding; solvent effects; gauche effect; glycols; ethylene glycol
Record Number:CaltechAUTHORS:20150930-125953201
Persistent URL:http://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:30 Sep 2015 21:14

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