The crystal and molecular structure of threitol

Kopf, Jürgen; Morf, Martina; Zimmer, Bärbel; Haupt, Erhard T. K.; Jarchow, O.; Köll, Peter

doi:10.1016/0008-6215(93)84246-3

Cited by 11 publications

(10 citation statements)

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“…The presence of four hydroxyl groups attached to different carbon atoms gives rise to a complex system of intermolecular and intramolecular hydrogen bonds, which play an important role in the molecular structure of these compounds and, therefore, in many properties of polyols, namely the sweetness, 1 hygroscopicity 2 and cryopreservation, 3,4 among others. Despite the existence of some published data concerning the solid state, [5][6][7][8][9][10][11][12] we are not aware of any theoretical or experimental data on the structure of erythritol and threitol in the gas state. The molecular flexibility and the presence of four OH groups result in a high number of possible conformations accounting for the energy of the isolated molecules.…”

Section: Introductionmentioning

confidence: 99%

Conformational study of erythritol and threitol in the gas state by density functional theory calculations

Jesus

Tomé

Rosado

et al. 2005

Carbohydrate Research

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Abstract-Density functional theory calculations using the B3LYP functional and the 6-311++G(d,p) basis set were carried out on the isolated molecules of erythritol and L L-threitol. For the meso isomer, a relatively large number of conformers have to be considered to describe the gas state structure. The lowest energy conformer is characterized by the establishment of a strong intramolecular H-bond between the two terminal hydroxyl groups, giving rise to a seven-membered ring and two additional weaker H-bonds between vicinal OH groups. In the case of L L-threitol, two conformers are predominant in the gas state, and both are stabilized by the formation of a cyclic system of four intramolecular hydrogen bonds involving all OH groups. The conformational stability in both diastereomers is discussed in terms of the electronic energy and of the Gibbs energy. The weighted mean enthalpy of both diastereomers in the gas state at 298.15 K was obtained from the thermodynamic data and Boltzmann populations of the low-energy conformers.

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Section: Introductionmentioning

confidence: 99%

Conformational study of erythritol and threitol in the gas state by density functional theory calculations

Jesus

Tomé

Rosado

et al. 2005

Carbohydrate Research

View full text Add to dashboard Cite

show abstract

“…As stated above, information on the crystal structure of both compounds from diffraction methods is available in literature [12,13]. A further stage in the structural characterization of these isomers can be achieved by complementing the diffraction data with the information taken from vibrational spectroscopy.…”

Section: Correlation Between the Spectral And Structural Datamentioning

confidence: 99%

“…In the case of L-threitol, the X-ray diffraction data reveal the existence of three crystallographically independent conformations in the unit cell (designated as I, II and III) [12]. There are only slight structural differences among them.…”

Section: Optimized Molecular Crystal Conformationsmentioning

confidence: 99%

“…The molecular conformations existent in the crystal structure, obtained from the X-ray [12] and neutron diffraction data [13], were used as starting structures to calculate the theoretical spectra. These conformations were fully optimized at the B3LYP/6-311++G(d, p) level of theory followed by harmonic frequencies calculations.…”

Section: Computational Calculationsmentioning

confidence: 99%

“…In the case of erythritol the non-optimized structure of conformation B is also shown. The starting conformations were obtained from the atomic coordinates given in references [13] and [12], for erythritol and L-threitol, respectively. particularly in the relative OH groups orientation, the calculated reference spectrum of erythritol to be compared with the experimental one was that of conformation A.…”

Section: Optimized Molecular Crystal Conformationsmentioning

confidence: 99%

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