Hartree-fock and density functional theory study of α-cyclodextrin conformers

Verónica Jiménez, Joel B. Alderete

Resultado de la investigación: Article

17 Citas (Scopus)

Resumen

Herein, we report the geometry optimization of four conformers of α-cyclodextrin (α-CD) by means of PM3, HF/STO-3G, HF/3-21G, HF/6-31G(d), B3LYP/6-31G(d), and X3LYP/6-31G(d) calculations. The analysis of several geometrical parameters indicates that all conformers possess bond lengths, angles, and dihedrals that agree fairly well with the crystalline structure of α-CD. However, only three of them (1-3) resemble the polar character of CDs and show intramolecular hydrogen-bonding patterns that agree with experimental NMR data. Among them, conformer 3 appears to be the most stable species both in the gas phase and in solution; therefore, it is expected to be the most suitable representative structure for α-CD conformation. The purpose of selecting such a species is to identify an appropriate structure to be employed as a starting point for reliable computational studies on complexation phenomena. Our results indicate that the choice of a particular α-CD conformer should affect the results of ab initio computational studies on the inclusion complexation with this cyclodextrin since both the direction and the magnitude of the dipole moment depend strongly on the conformation of α-CD.

Idioma originalEnglish
Páginas (desde-hasta)672-685
Número de páginas14
PublicaciónJournal of Physical Chemistry A
Volumen112
N.º4
DOI
EstadoPublished - 31 ene 2008

Huella dactilar

Cyclodextrins
Complexation
Density functional theory
Conformations
dipole moments
inclusions
vapor phases
density functional theory
nuclear magnetic resonance
optimization
Dipole moment
Bond length
hydrogen
geometry
Hydrogen bonds
Gases
Nuclear magnetic resonance
Crystalline materials
Geometry
Direction compound

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Citar esto

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abstract = "Herein, we report the geometry optimization of four conformers of α-cyclodextrin (α-CD) by means of PM3, HF/STO-3G, HF/3-21G, HF/6-31G(d), B3LYP/6-31G(d), and X3LYP/6-31G(d) calculations. The analysis of several geometrical parameters indicates that all conformers possess bond lengths, angles, and dihedrals that agree fairly well with the crystalline structure of α-CD. However, only three of them (1-3) resemble the polar character of CDs and show intramolecular hydrogen-bonding patterns that agree with experimental NMR data. Among them, conformer 3 appears to be the most stable species both in the gas phase and in solution; therefore, it is expected to be the most suitable representative structure for α-CD conformation. The purpose of selecting such a species is to identify an appropriate structure to be employed as a starting point for reliable computational studies on complexation phenomena. Our results indicate that the choice of a particular α-CD conformer should affect the results of ab initio computational studies on the inclusion complexation with this cyclodextrin since both the direction and the magnitude of the dipole moment depend strongly on the conformation of α-CD.",
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Hartree-fock and density functional theory study of α-cyclodextrin conformers. / Jiménez, Verónica; Alderete, Joel B.

En: Journal of Physical Chemistry A, Vol. 112, N.º 4, 31.01.2008, p. 672-685.

Resultado de la investigación: Article

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AB - Herein, we report the geometry optimization of four conformers of α-cyclodextrin (α-CD) by means of PM3, HF/STO-3G, HF/3-21G, HF/6-31G(d), B3LYP/6-31G(d), and X3LYP/6-31G(d) calculations. The analysis of several geometrical parameters indicates that all conformers possess bond lengths, angles, and dihedrals that agree fairly well with the crystalline structure of α-CD. However, only three of them (1-3) resemble the polar character of CDs and show intramolecular hydrogen-bonding patterns that agree with experimental NMR data. Among them, conformer 3 appears to be the most stable species both in the gas phase and in solution; therefore, it is expected to be the most suitable representative structure for α-CD conformation. The purpose of selecting such a species is to identify an appropriate structure to be employed as a starting point for reliable computational studies on complexation phenomena. Our results indicate that the choice of a particular α-CD conformer should affect the results of ab initio computational studies on the inclusion complexation with this cyclodextrin since both the direction and the magnitude of the dipole moment depend strongly on the conformation of α-CD.

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