Molecular structure and barrier to internal rotation of gaseous glycolic acid

Iijima, Kinya; Katô, Makoto; Beagley, B.

doi:10.1016/0022-2860(93)85027-r

Cited by 15 publications

(19 citation statements)

References 5 publications

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“…Simple a-hydroxy carboxylic acids, in particular, have been extensively studied, both theoretically and experimentally [7][8][9][10][11][12]. On the other hand, their methyl esters have not been paid so much attention.…”

Section: Introductionmentioning

confidence: 99%

Matrix isolation FTIR spectroscopic and theoretical study of methyl lactate

Borba

Gómez‐Zavaglia

Lapiński

et al. 2004

Vibrational Spectroscopy

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Methyl lactate [CH(CH 3)OHC(¼O)OCH 3 ] conformational space was investigated by extensive DFT/B3LYP/6-311þþG(d,p) and MP2/6-31þþG(d,p) calculations and matrix-isolation FTIR spectroscopy in argon and xenon matrices. From the seven different conformers predicted by the calculations, two forms (the most stable conformers yielded by the calculations: SsC and GskC, where the letters refer to the conformations assumed by the HOCC, OCC¼O and O¼COC dihedrals, respectively) were observed and characterized spectroscopically. Conformer interconversion pathways were also theoretically investigated. The low calculated barrier associated with the G 0 sk 0 C ! GskC conversion ($1 kJ mol À1) explains the absence of the third most stable form (G 0 sk 0 C) of methyl lactate in low-temperature matrices. Deposition of methyl lactate at different temperatures, together with the theoretical data, aided to the full assignment of the observed spectra. #

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Section: Introductionmentioning

confidence: 99%

Matrix isolation FTIR spectroscopic and theoretical study of methyl lactate

Borba

Gómez‐Zavaglia

Lapiński

et al. 2004

Vibrational Spectroscopy

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“…The rotamers of glycolic acid have been studied both experimentally [8][9][10][11][12] and theoretically. 9,[11][12][13][14][15][16] Eight distinct rotamers have been identified.…”

Section: Introductionmentioning

confidence: 99%

Clusters of glycolic acid with three to six water molecules

Roy

Hu²,

Thakkar³

2005

The Journal of Chemical Physics

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Semiempirical, ab initio, and density functional theory calculations are used to locate many low-energy minima on the potential energy surfaces of the CH2OHCOOH-(H2O)n complexes with n = 3,4,5,6. In the clusters with three, four, and five water molecules, the lowest-energy structure consists of a (H2O)n complex, not necessarily of lowest energy, hydrogen bonded to the carboxylic group of the glycolic acid. The lowest-energy structure for n = 6 is similar except that the water hexamer is hydrogen bonded to both the carboxylic and alpha-hydroxyl groups of the acid. In all the lowest-energy clusters, the intramolecular hydrogen bond remains intact in the glycolic acid.

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“…Being the simplest member of this family of molecules, glycolic acid is by far the most studied a-hydroxy acid, both experimentally and theoretically [7][8][9][10][11][12][13][14][15]. However, its methyl ester has not been paid much attention.…”

Section: Introductionmentioning

confidence: 99%

Molecular structure and vibrational spectra of methyl glycolate and methyl α-hydroxy isobutyrate

Jarmelo

Fausto

1999

Journal of Molecular Structure

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Conformational isomerism in isolated and liquid methyl glycolate and methyl a-hydroxy isobutyrate was investigated by a concerted molecular orbital and vibrational spectroscopic approach (infrared and Raman). The molecular structures, relative energies, dipole moments and vibrational spectra of the various possible conformers of the studied compound were calculated, using the extended 6-31G* basis set at the HF-SCF ab initio level of theory. The theoretical results were then used to interpret infrared and Raman data obtained under different experimental conditions. It was found that both in the liquid and gaseous phase the studied molecules exist in two experimentally observed conformational states, the C s point group Syn-syn conformer (Ss), which exhibits an intramolecular OH … Oy hydrogen bond, being the most stable form. As expected, the relative populations of the second more stable conformers increase in the liquid phase, since intermolecular interactions tend to reduce the importance of the intramolecular H-bonding that is the main stabilizing factor of the Ss forms.

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Molecular structure and barrier to internal rotation of gaseous glycolic acid

Cited by 15 publications

References 5 publications

Matrix isolation FTIR spectroscopic and theoretical study of methyl lactate

Matrix isolation FTIR spectroscopic and theoretical study of methyl lactate

Clusters of glycolic acid with three to six water molecules

Molecular structure and vibrational spectra of methyl glycolate and methyl α-hydroxy isobutyrate

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