Conformational studies of ethylene glycol and its two methyl ether derivatives

Podo, Franca; Némethy, George; Indovina, Pietro Luigi; Radics, L.; Viti, Vincenza

doi:10.1080/00268977400100471

Cited by 61 publications

(44 citation statements)

References 43 publications

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“…Most significantly for the discussion here is the degree to which the preferences should be interpreted as the result of strong intramolecular hydrogen bonding between hydroxyl groups, especially when the geometries of such hydrogen bonds would not seem to be very favorable. Some representative pro examples involve infrared and Raman, 1 microwave, 2 electron and neutron diffraction, 3,4 molecular dynamics 5,6 and quantum calculations, 7,8 whereas con examples include infrared and Raman, 9 -13 molecular dynamics 5,6,14 and quantum calculations. 15 -17 This is an area where NMR can be expected to provide important information.…”

Section: Introductionmentioning

confidence: 99%

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

Petterson

Stein

Drake

et al. 2005

Magnetic Reson in Chemistry

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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.

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Section: Introductionmentioning

confidence: 99%

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

Petterson

Stein

Drake

et al. 2005

Magnetic Reson in Chemistry

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“…[1][2][3][4][5] However, the conformational preferences of DME, and in particular the magnitude of the C-C gauche preference ("gauche effect"), remains somewhat controversial. Theoretical work done by several groups has demonstrated that both a reasonably large basis set (with diffuse and/or polarization functions) and electron correlation correction are necessary to accurately represent the relative energies of the DME conformers.…”

Section: Introductionmentioning

confidence: 99%

Conformations of 1,2-Dimethoxyethane in Gas and Solution Phase from Molecular Mechanics and Monte Carlo/Stochastic Dynamics Simulations

and

Hall

1996

J. Phys. Chem.

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The conformations and energies of 1,2-dimethoxyethane (DME) are estimated using molecular mechanics and Monte Carlo/stochastic dynamics (MC/SD) simulations. The torsional parameters of the Amber* and OPLS* force fields were modified to reproduce high-level ab initio data describing DME conformer energies in the gas phase. Predicted conformer populations from gas-phase molecular mechanics and simulations are in agreement with theoretical calculations and with previous electron diffraction data. For simulations in chloroform and aqueous solution an implicit solvation model (GB/SA) was used. The GB/SA treatment gives the TGT as the most populated conformer in aqueous solution, providing the major contribution to the observed gauche effect around the C-C dihedral. Significantly, the energy of the TGT conformer is lower than that of the TTT structure in solution, and it is stabilized relative to the TGG′ conformer. These results are compared to previous work in solution and in vacuo and with ab initio results.

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“…Thus it was thought interesting to study aqueous solutions of glycol ethers as they contain oxygen (-O-) and hydroxyl (-OH) functional groups in the same molecule which allow self association via inter-and intra-molecular hydrogen bonding. Different spectroscopic and computational techniques have been used to investigate the existence of inter-and intra-molecular hydrogen bonding in glycol ethers in pure form as well as in the mixtures [1][2][3][4][5][6][7][8][9][10][11]. Glycol ethers are produced in large quantities worldwide and are industrially important solvents.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic and optical studies of some ethylene glycol ethers in aqueous solutions at T=298.15K

Dhondge¹,

Pandhurnekar²,

Parwate³

2009

The Journal of Chemical Thermodynamics

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Conformational studies of ethylene glycol and its two methyl ether derivatives

Cited by 61 publications

References 43 publications

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

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

Conformations of 1,2-Dimethoxyethane in Gas and Solution Phase from Molecular Mechanics and Monte Carlo/Stochastic Dynamics Simulations

Thermodynamic and optical studies of some ethylene glycol ethers in aqueous solutions at T=298.15K

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