An NMR investigation of the importance of intramolecular hydrogen bonding in determining the conformational equilibrium of ethylene glycol in solution.
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.
Petterson
Krag A
KA
Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, California 91125, USA.
Stein
Robin S
RS
Drake
Michael D
MD
Roberts
John D
JD
D000465:Algorithms; D002247:Carbon Isotopes; D019855:Ethylene Glycol / Q000032:analysis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008968:Molecular Conformation; D044367:Phase Transition; D011522:Protons; D012997:Solvents / Q000737:chemistry*
D002247:Carbon Isotopes; D011522:Protons; D012997:Solvents; D019855:Ethylene Glycol