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

被引:55
作者
Petterson, KA
Stein, RS
Drake, MD
Roberts, JD [1 ]
机构
[1] CALTECH, Lab Chem, Pasadena, CA 91001 USA
[2] CALTECH, Gates & Crellin Labs Chem, Pasadena, CA 91001 USA
关键词
NMR; HNMR; C-13; conformational analysis; intramolecular hydrogen bonding; solvent effects; gauche effect; glycols; ethylene glycol;
D O I
10.1002/mrc.1512
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 (C) 2005 John Wiley Sons, Ltd.
引用
收藏
页码:225 / 230
页数:6
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