Crystal and Molecular Structure of 1,2-Dimethoxyethane Crystallized on a New Diffractometer

Yokoyama, Yoshihiro; Uekusa, Hidehiro; Ohashi, Yuji

doi:10.1246/cl.1996.443

Cited by 16 publications

(19 citation statements)

References 2 publications

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“…The crystal structure of G1 is known in which the G1 molecules adopt one of two conformations (tg + t or tg -t). 33 Solvate Structures and Ionic Association. In dilute solutions, electrolyte mixtures are typically modeled as consisting of highly solvated "free" ions.…”

Section: Resultsmentioning

confidence: 99%

Glyme−Lithium Salt Phase Behavior

2006

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Phase diagrams are reported for glyme mixtures with simple lithium salts. The glymes studied include monoglyme (DME), diglyme, triglyme, and tetraglyme. The lithium salts include LiBETI, LiAsF6, LiI, LiClO4, LiBF4, LiCF3SO3, LiBr, LiNO3, and LiCF3CO2. The phase diagrams clearly illustrate how solvate formation and thermophysical properties are dictated by the ionic association strength of the salt (i.e., the properties of the anions) and chain length of the solvating molecules. This information provides critical predictive capabilities for solvate formation and ionic interactions common in organometallic reagents and battery electrolytes.

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Section: Resultsmentioning

confidence: 99%

Glyme−Lithium Salt Phase Behavior

2006

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“…The geometries of the conformers of DME have been calculated previously, − but no comparative discussions of the results by different calculation methods have been made. The calculated results may be compared with the experimental molecular geometries in crystals determined by X-ray diffraction; the molecule in crystals has been shown to assume the TGT conformation.…”

Section: Resultsmentioning

confidence: 99%

“…It is noticed that the CO−CC torsion angle in crystals differs by 7−8° from the angle theoretically calculated, apparently due to intermolecular interactions. The X-ray diffraction study has in fact shown the possibility of intermolecular interactions between the methyl group and the oxygen atom and between the methylene group and the oxygen atom …”

Section: Resultsmentioning

confidence: 99%

Density Functional Study of the Conformations and Vibrations of 1,2-Dimethoxyethane

Yoshida

Matsuura

1998

J. Phys. Chem. A

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The conformations and vibrations of 1,2-dimethoxyethane (DME) have been studied by density functional theory (DFT) in comparison with the molecular orbital (MO) methods. The calculations using the 6-31G* basis set were performed by five DFT methods (BVWN, BP86, BLYP, B3PW91, and B3LYP) and two MO methods (HF and MP2). The energies of conformers were better predicted by the DFT methods using the B3 exchange functional than other methods. The vibrational wavenumbers calculated by the DFT and MO methods explained, after correcting with uniform scaling, the observed Raman and infrared spectra of the normal and perdeuterated species of DME. It was confirmed that the conformer of DME present in the solid state is TGT, and the conformers in the liquid state are TGT, TTT, TGG‘, and TTG. The present calculations further indicated that the TGG and GGG conformers are also present in the liquid state. The distributions of the ratio of the unscaled calculated wavenumber to the experimental wavenumber are narrower with the B3PW91 and B3LYP methods than with other methods, indicating that these two methods, when making appropriate uniform scaling corrections, give wavenumbers in excellent agreement with the experimental wavenumbers. In conclusion, the performance of the B3PW91 and B3LYP methods is the best among the DFT and MO methods used in this work in reproducing the experimental results of the energies, molecular geometries, and vibrational wavenumbers for DME.

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“…In the crystalline state DME does not pack in the usual side-by-side zigzag conformation preferred by the corresponding alkane (hexane) but rather in gauche conformations that expose the lone electron pairs of the two oxygen atoms towards the same direction. 20 The packing of diglyme in a crystalline phase is also not dominated by zig-zag (transoid) conformations or side-by-side arrangements but rather by an assortment of trans and gauche conformations, as attested by vibrational-dynamics and first-principle studies. 21 Such differences between DME or diglyme and the corresponding alkanes (hexane or nonane) in terms of chain-chain interactions may partially explain the different bulkiness of the observed non-polar domains.…”

Section: Molecular Dynamics Simulationsmentioning

confidence: 99%

Nano-segregation in ionic liquids: scorpions and vanishing chains

Shimizu¹,

Bernardes²,

Triolo

et al. 2013

Phys. Chem. Chem. Phys.

124

141

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The present study analyses the large structural differences, first observed using X-ray diffraction, between 1-alkyl-3-methylimidazolium-based ionic liquids, [Cnmim][Ntf2] (n = 3, 6, 9), and their counterparts with ether-substituted alkyl side chains, [(C1OC1)(n/3)mim][Ntf2] (n = 3, 6, 9). The MD simulations-obtained using a non-polarizable atomistic force-field to model the ionic liquids under discussion-demonstrate that the suppression of the nanostructured nature in the ionic liquids with ether chains is persistent along the entire series and it is not due to any modification of the polar network of the ionic liquid but rather due to the different morphologies of the non-polar regions that surround it. The modification of the non-polar regions-shift from bulky segregated domains in [Cnmim][Ntf2] to thin enveloping ones in [(C1OC1)(n/3)mim][Ntf2]-are caused by the inability of the oxygen-substituted alkyl side chains to pack effectively side by side, the existence of kinks along the chain that lead eventually to intra-molecular, scorpion-like interactions between the chains and the imidazolium ring, and by their stronger interactions with the cations of the polar network via the lone electron pairs of the ether oxygen atoms.

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Crystal and Molecular Structure of 1,2-Dimethoxyethane Crystallized on a New Diffractometer

Cited by 16 publications

References 2 publications

Glyme−Lithium Salt Phase Behavior

Glyme−Lithium Salt Phase Behavior

Density Functional Study of the Conformations and Vibrations of 1,2-Dimethoxyethane

Nano-segregation in ionic liquids: scorpions and vanishing chains

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