DFT and neutron diffraction study of 1,6-anhydro-β-D-glucopyranose (levoglucosan)

• Authors: Mariana Sládkovic̆ová , Pavel Mach , L’ubomír Smrc̆ok , Håkan Rundlöf
• Languages of publication: EN

Abstracts

EN

Geometries of 27 generated conformers of levoglucosan were optimized in vacuo at DFT level of theory combining several functionals with high quality basis sets. For the sake of comparison a reference molecular and crystal geometry obtained from 30 K single crystal neutron diffraction data was used. Analysis of the conformers’ geometries revealed that in all stable conformers intramolecular two-or three centre hydrogen bonds were formed. Relative energy of the conformer, which approximated the molecule in the crystal structure the most, was only ∼3 kcal/mol higher, than the energy of the most stable conformer in vacuo. The largest discrepancies between the geometries calculated in vacuo and experimental geometry concentrated in the vicinity of anomeric C1. These differences were reduced by involving O1 to intermolecular hydrogen bond using a simple model of the respective hydrogen bond in the crystal. [...]

Keywords

EN

Levoglucosan; DFT; neutron diffraction; hydrogen bonding; ring strain; anomeric effect; conformational analysis

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2007
• Volume: 5
• Issue: 1
• Pages: 55-70

Dates

published

1 - 3 - 2007

online

1 - 3 - 2007

Contributors

author

Mariana Sládkovic̆ová

• Institute of Inorganic Chemistry, Slovak Academy of Sciences, SK-845 36, Bratislava, Slovak Republic

author

Pavel Mach

• Institute of Inorganic Chemistry, Slovak Academy of Sciences, SK-845 36, Bratislava, Slovak Republic

author

L’ubomír Smrc̆ok

• Institute of Inorganic Chemistry, Slovak Academy of Sciences, SK-845 36, Bratislava, Slovak Republic

author

Håkan Rundlöf

• Institutionen för materialkemi, Uppsala Universitet, Box 538, 751 21, Uppsala, Sweden

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Identifiers

DOI

10.2478/s11532-006-0058-5