Crystal structures of ethylene glycol and ethylene glycol monohydrate

Fortes, A. Dominic; Suard, Emmanuelle

doi:10.1063/1.3668311

Cited by 35 publications

(24 citation statements)

References 65 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The pronounced heterochiral stability predicted for ED dimers and trimers is in stark contrast to the solid state structure, which consists of homochiral monomer units with the same conformation as in the gas phase. 8,77 Solid ED is thus an elementary representative of the rare class 6 of conglomerate formers, but somewhat surprisingly and very interestingly it still prefers heterochiral aggregation on the nanometer scale.…”

Section: Discussionmentioning

confidence: 99%

“…At first glance, this is nicely parallel to ED, which is a conglomerate former when crystallised. 8 However, in the case of CD there is evidence in the literature that the racemic form is more stable and thus less volatile. 17 Therefore, the concentration probed in the jet is more likely a consequence of different effective contact areas in the sample pickup.…”

Section: Paper Pccpmentioning

confidence: 99%

“…This can have interesting consequences in the solid. E.g., the simplest 1,2-diol, HO-CH 2 -CH 2 -OH, crystallises in separate left-handed and right-handed, extended hydrogen-bonded networks, 8 although its chirality is only transient in the liquid.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The reduced cohesion of homoconfigurational 1,2-diols

Hartwig

Lange

Poblotzki

et al. 2020

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

By a combination of linear FTIR and Raman jet spectroscopy, racemic trans-1,2-cyclohexanediol is shown to form an energetically unrivalled S 4 -symmetric heterochiral dimer in close analogy to 1,2-ethanediol.Analogous experiments with enantiopure trans-1,2-cyclohexanediol reveal the spectral signature of at least three unsymmetric homochiral dimers. A comparison to signal-enhanced spectra of 1,2-ethanediol and to calculations uncovers at least three transiently homochiral dimer contributions as well. In few of these dimer structures, the intramolecular OHÁ Á ÁO contact present in monomeric 1,2-diols survives, despite the kinetic control in supersonic jet expansions. This provides further insights into the dimerisation mechanism of conformationally semi-flexible molecules in supersonic jets. Racemisation upon dimerisation is shown to be largely quenched under jet cooling conditions, whereas it should be strongly energy-driven at higher temperatures. The pronounced energetic preference for heterochiral aggregation of vicinal diols is also discussed in the context of chirality-induced spin selectivity. † Electronic supplementary information (ESI) available: Interactive and static structures, tables of experimental and computational details, energy diagrams for different levels of calculation, and additional experimental spectra. See

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Paper Pccpmentioning

confidence: 99%

See 1 more Smart Citation

The reduced cohesion of homoconfigurational 1,2-diols

Hartwig

Lange

Poblotzki

et al. 2020

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

show abstract

“…Many papers have been published that quote the original microwave experiment of Bastiansen [39], for instance [53][54][55][56][57][58][59][60][61][62][63][64][65]. However, we were unable to find any precise determination of the experimental geometry in gas phase.…”

Section: Insert Figurementioning

confidence: 73%

Computational Evidence Suggests That 1-Chloroethanol May Be an Intermediate in the Thermal Decomposition of 2-Chloroethanol into Acetaldehyde and HCl

et al. 2019

View full text Add to dashboard Cite

The dehalogenation of 2-chloroethanol (2ClEtOH) in gas phase with and without participation of catalytic water molecules has been investigated using methods rooted into the density functional theory. The well-known HCl elimination leading to vinyl alcohol (VA) was compared to the alternative elimination route towards oxirane and shown to be kinetically and thermodynamically more favorable. However, the isomerization of VA to acetaldehyde in the gas phase, in the absence of water, was shown to be kinetically and thermodynamically less favorable than the recombination of VA and HCl to form the isomeric 1-chloroethanol (1ClEtOH) species. This species is more stable than 2ClEtOH by about 6 kcal mol -1 -1 ). Thus, it is concluded that while 1ClEtOH may be a plausible intermediate in the gas phase dehalogenation of 2ClEtOH, it is unlikely that it plays a major role in water complexes (or, by inference, aqueous solution). It is also shown that neither in the gas phase nor in the cluster with one water molecule, the oxirane path is competitive with the VA alcohol path.

show abstract

“…These investigations suggest that the liquid structure is dominated by a hydrogen-bonded network with a mean number of hydrogen bonds per molecule slightly lower than four, independently of the potential model used. The structure of the isolated ethylene glycol molecule has been studied experimentally by electron diffraction [10] as well as by microwave [11] and infrared spectroscopic methods in the gas phase/low-temperature matrix [12][13], whereas the strong structural correlations of condensed-phase EG were investigated by diffraction techniques (X-Ray and neutron [14]) in the liquid, focusing in particular on the structure of the most stable dimers, and in the solid state by neutron diffraction [15]. As far as the liquid structure is concerned, infrared and Raman spectra suggest that almost all OH groups are involved in inter-and intramolecular H-bonds [16,17].…”

Section: Introductionmentioning

confidence: 99%

New Insights Into the Structure of Hydroxylated and Alkylated Glycols: A Comparative X-ray Diffraction, Raman and Molecular Dynamics Study of Ethane-1,2-Diol, 2-Methoxyethan-1-ol and 1,2-Dimethoxy Ethane

Gontrani¹,

Tagliatesta²,

Agresti³

et al. 2020

Preprint

View full text Add to dashboard Cite

In this study, we report a detailed experimental and theoretical investigation of three glycols, namely ethane-1,2-diol, 2-methoxyethan-1-ol and 1,2-dimethoxy ethane. For the first time, the X-Ray spectra of the latter two liquids was measured at room temperature, and they were compared with the newly measured spectrum of ethane-1,2-diol. The experimental diffraction patterns were interpreted very satisfactorily with molecular dynamics calculations, and suggest that in liquid ethane-1,2-diol most molecules are found in gauche conformation, with intramolecular hydrogen bond between the two hydroxyl groups. Intramolecular H-bonds are established in the mono-alkylated diol, but the interaction is weaker. The EDXD study also evidences strong intermolecular hydrogen-bond interactions, with short O···O correlations in both systems, while longer methyl-methyl interactions are found in 1,2-dimethoxy ethane. X-Ray studies are complemented by micro Raman investigations at room temperature and at 80°C, that confirm the conformational analysis predicted by X-Ray experiments and simulations.

show abstract

Crystal structures of ethylene glycol and ethylene glycol monohydrate

Cited by 35 publications

References 65 publications

The reduced cohesion of homoconfigurational 1,2-diols

The reduced cohesion of homoconfigurational 1,2-diols

Computational Evidence Suggests That 1-Chloroethanol May Be an Intermediate in the Thermal Decomposition of 2-Chloroethanol into Acetaldehyde and HCl

New Insights Into the Structure of Hydroxylated and Alkylated Glycols: A Comparative X-ray Diffraction, Raman and Molecular Dynamics Study of Ethane-1,2-Diol, 2-Methoxyethan-1-ol and 1,2-Dimethoxy Ethane

Contact Info

Product

Resources

About