The molecular structure of 1,3-propanediol in the gas phase, an electron diffraction study

Kinneging, A. J.; Mom, V.; Mijlhoff, F.C.; Renes, G.

doi:10.1016/0022-2860(82)80042-2

Cited by 26 publications

(15 citation statements)

References 1 publication

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“…Many workers have studied intramolecular solvation, and the phenomenon has been characterized both theoretically and experimentally in gaseous ionic species such as diols, , diamines, − polyamines, diethers, , diketones, , amides and amino acid derivatives, amino alcohols, diaminonaphthalenes, carboxylic acid derivatives, and methoxyalcohols − and diols. ,,− It has been demonstrated for chloroalkylnitriles that intramolecular solvation stabilizes the transition state of S N 2 reactions . Besides mass spectrometric methods, intramolecular solvation has been studied with a variety of other experimental methods such as microwave spectroscopy, gas-phase electron diffraction, and IR, Raman, and NMR 24 spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Solvation of Carboxylate Anions in the Gas Phase

Norrman

McMahon

1999

J. Phys. Chem. A

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Proton exchange reactions between acetate, n-butanoate, 2-ethylhexanoate, and n-decanoate were studied experimentally by the use of PHPMS and theoretically by the use of ab initio methods. The occurrence of a curvature in some of the van't Hoff plots suggests isomerization of at least one of the participants in the equilibrium. This isomerization is suggested to be an intramolecular solvation of the carboxylate anions via unconventional hydrogen bonding. These interactions are discussed in terms of charge distributions in the unfolded and folded conformers of the carboxylates. Thermochemical values for the intramolecular solvation were deconvoluted from the curved van't Hoff plots by a fitting procedure. The thermochemical data for the intramolecular solvation was used to calculate the conformer composition of the carboxylate anions. Various properties related to the intramolecular solvation of the carboxylate anions are discussed.

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Section: Introductionmentioning

confidence: 99%

Intramolecular Solvation of Carboxylate Anions in the Gas Phase

Norrman

McMahon

1999

J. Phys. Chem. A

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“…Ab initio studies (Bultinck et al, 1995;Vazquez et al, 1988) based on the HF and MP2 calculactions have shown that the lowest energy conformers have gauche heavy-atom torsions, and that they are stabilized by intramolecular hydrogen bonding. The existence of intramolecular hydrogen bonds was also confirmed by gas-phase electron diffraction (GED) (Kinneging et al, 1982;Traetteberg & Hedberg, 1994). The results have shown that the molecule of 1,3 -propanediol exists exclusively in G+G-conformation with OH groups in 1,3 parallel positions nearly ideally placed to form an intramolecular hydrogen bond.…”

Section: Modeling Of Volumetric Properties Of Organic Mixtures Based mentioning

confidence: 84%

“…GED study of 1,3-propanediol (Kinneging et al, 1982) shows that the molecules exist in +gauche-gauche conformation (G+G-) with 1,3 parallel OH groups.…”

Section: Alcohol + Chloroformmentioning

confidence: 99%

Modeling of Volumetric Properties of Organic Mixtures Based on Molecular Interactions

Kijevčanin¹,

Djordjević²,

Radović³

et al. 2012

Molecular Interactions

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“…3. It is important to point out that the initial value of the O2-H1-O5 angle, in the pm conformer is 106.51, which can be considered too small when compared with the experimental values obtained for well known O-HÁ Á ÁO systems such as b-diketone enols 18 (152.3) and ethylene glycol 19 (156.01). The O-HÁ Á ÁO angle in the most stable conformer of ethylene glycol at the B3LYP/6-311þþG(2d,2p) level yielded 137.61.…”

Section: Methodology and Some Geometrical And Energy Featuresmentioning

confidence: 93%

Topological study of intramolecular hydrogen bonding in β-hydroxyethylperoxy radical and β-hydroxyethoxy radical along its dissociation pathway

Mandado¹,

Mosquera²,

Alsenoy³

2005

Phys. Chem. Chem. Phys.

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The presence of intramolecular hydrogen bond (IHB) in beta-hydroxyethylperoxy and beta-hydroxyethoxy radicals was investigated using the QTAIM topological study on UB3LYP/6-311++G(2d,2p) charge densities. Only one of the two conformers of beta-hydroxyethylperoxy radical which were previously considered to present IHB displays a bond critical point (BCP) associated to an IHB. Furthermore, the atomic energies and electron populations indicate no evidence of IHB in the second conformer. Nevertheless, very small differences in molecular energies were obtained using several one-step and multi-step methods (G3, G3B3) between both conformers. No BCP is found between the hydroxyl hydrogen and the oxygen in the most stable conformer or in the transition state for the dissociation path of beta-hydroxyethoxy radical. However, a BCP is formed in the last steps of this path, thereby yielding H-bonded products.

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The molecular structure of 1,3-propanediol in the gas phase, an electron diffraction study

Cited by 26 publications

References 1 publication

Intramolecular Solvation of Carboxylate Anions in the Gas Phase

Intramolecular Solvation of Carboxylate Anions in the Gas Phase

Modeling of Volumetric Properties of Organic Mixtures Based on Molecular Interactions

Topological study of intramolecular hydrogen bonding in β-hydroxyethylperoxy radical and β-hydroxyethoxy radical along its dissociation pathway

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