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An NMR investigation of the importance of intramolecular hydrogen bonding in determining the conformational equilibrium of ethylene glycol in solution
Author(s) -
Petterson Krag A.,
Stein Robin S.,
Drake Michael D.,
Roberts John D.
Publication year - 2005
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1512
Subject(s) - chemistry , intramolecular force , ethylene glycol , chloroform , hydrogen bond , aqueous solution , proton nmr , nuclear magnetic resonance spectroscopy , organic chemistry , molecule
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. Copyright © 2005 John Wiley & Sons, Ltd.