Global Conformational Analysis of 1,2-Ethanediol

Yeh, Tai-Sheng; Chang, Ying-Pin; Su, Tingwei; Chao, Ito

doi:10.1021/j100087a018

Cited by 46 publications

(60 citation statements)

References 10 publications

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“…Thesurprising aspect in the almost exclusive formation of the 4H dimer structure from two monomer units is not so much the rearrangement of four OH torsional angles,which is facilitated by quantum tunneling.Itisthe forced inversion of the OCCO torsional angle upon aggregation in close to 50 % of all encounters,aprocess which is known to be strongly hindered in monomeric jet expansions of the related 1,2dimethylglycol. [43] Forethylene glycol, the required barrier is Angewandte Chemie Communications close to 20 kJ mol À1 [44] (see also Figure S4), too high to be overcome by carrier gas collisions.I nt he dimer,i ti s conceivable that this barrier is lowered. Indeed, we find that the transition state from the lowest CC-homochiral dimer (3Hb) to the CC-heterochiral global minimum structure only requires 14.0 kJ mol À1 of activation and passes through aCChomochiral dimer with four hydrogen bonds ( Figure S6).…”

Section: Angewandte Chemiementioning

confidence: 99%

A Symmetric Recognition Motif between Vicinal Diols: The Fourfold Grip in Ethylene Glycol Dimer

2016

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Ethylene glycol has a transiently chiral, asymmetric global minimum structure, but it favors a highly symmetric, achiral dimer arrangement which has not been considered or found in previous quantum‐chemical studies. Complementary FTIR and Raman spectroscopy in supersonic jets allows for the detection and straightforward assignment of this four‐fold hydrogen‐bonded dimer, which introduces an interesting supramolecular binding motif for vicinal diols and provides a strong case for transient chirality synchronization.

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Section: Angewandte Chemiementioning

confidence: 99%

A Symmetric Recognition Motif between Vicinal Diols: The Fourfold Grip in Ethylene Glycol Dimer

2016

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“…Quantum-mechanical calculations for the model systems ethane-1,2-diol (Yeh et al, 1994) and pinacol (2,2-dimethylbutane-2,3-diol; Dahlqvist et al, 1998) indicate that the best gauche conformer (OÐCÐCÐO 9 60 ) is ca. 8 kJ mol À1 lower in energy than the best trans conformer (OÐCÐCÐ O 9 180 ) because of the weak intramolecular OÐHÁ Á ÁO bond that is possible in the former.…”

Section: Gauche Conformers Predominatementioning

confidence: 99%

Crystal packing in vicinal diols C _n H_m(OH)₂

Brock

2002

Acta Crystallogr Sect B

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The O-HtriplebondO bonds in vic-diols C(n)H(m)(OH)(2) have been studied using data retrieved from the Cambridge Structural Database. About half of these diols form complete, or almost complete, sets of intermolecular O-HtriplebondO bonds (i.e. two satisfied donors per molecule). For this half of the structures the frequencies of high-symmetry space groups and of structures with Z' > 1 (more than one molecule in the asymmetric unit) are substantially elevated. The most common motif among fully bonded structures is an R(2)(2)(10) dimer, which can be linked in a variety of ways to form one-, two- or even three-dimensional patterns. Most of the other half of the vic-diols form simple O-HtriplebondO chains in which each OH group participates in only one intermolecular hydrogen bond. The space-group frequencies for this second group of structures are unexceptional. The most important factor determining the extent of O-HtriplebondO bond formation is the degree of substitution of the vic-diol. The spatial segregation of OH groups that is necessary for the formation of O-HtriplebondO bonds is found to make the dense filling of space more difficult because the intermolecular spacings that are appropriate for the O-HtriplebondO bonds may be inappropriate for the rest of the molecule.

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“…Numerous studies have established that ethylene glycol (EG) molecules can have ten major conforma tions [1][2][3][4][5][6][7][8][9][10]. At the same time, only some of them are stabilized by intramolecular hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

Intra- and intermolecular hydrogen bonds in ethylene glycol, monoethanolamine, and ethylenediamine

Krest’yaninov

Titova

Zaichikov

2014

Russ. J. Phys. Chem.

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The structures of ethylene glycol, aminoethanol, ethylenediamine, and their dimers with the for mation of hydrogen bonds of different types are optimized by density functional theory (DFT) using hybrid functional B3LYP in the basis of 6 31++G(d,p), 6 311++G(2d,2p) and aug CC pVTZ. Energies of interac tions, hydrogen bond parameters, and oscillation frequency are calculated, and NBO analysis is performed. The types of hydrogen bonds formed in dimers of 1,2 disubstituted ethanes X-CH 2 -CH 2 -Y (X, Y = OH, NH 2 ) are established. Keywords: ethylene glycol, aminoethanol, ethylenediamine, intro and intermolecular hydrogen bonds, quan tum chemical methods of calculation.

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Global Conformational Analysis of 1,2-Ethanediol

Cited by 46 publications

References 10 publications

A Symmetric Recognition Motif between Vicinal Diols: The Fourfold Grip in Ethylene Glycol Dimer

A Symmetric Recognition Motif between Vicinal Diols: The Fourfold Grip in Ethylene Glycol Dimer

Crystal packing in vicinal diols C _n H_m(OH)₂

Intra- and intermolecular hydrogen bonds in ethylene glycol, monoethanolamine, and ethylenediamine

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Global Conformational Analysis of 1,2-Ethanediol

Cited by 46 publications

References 10 publications

A Symmetric Recognition Motif between Vicinal Diols: The Fourfold Grip in Ethylene Glycol Dimer

A Symmetric Recognition Motif between Vicinal Diols: The Fourfold Grip in Ethylene Glycol Dimer

Crystal packing in vicinal diols C n H m (OH)2

Intra- and intermolecular hydrogen bonds in ethylene glycol, monoethanolamine, and ethylenediamine

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Crystal packing in vicinal diols C _n H_m(OH)₂