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formerly Central European Journal of Chemistry

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

1Institute of Inorganic Chemistry, Slovak Academy of Sciences, SK-845 36, Bratislava, Slovak Republic

2Institutionen för materialkemi, Uppsala Universitet, Box 538, 751 21, Uppsala, Sweden

© 2005 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. (CC BY-NC-ND 3.0)

Citation Information: Open Chemistry. Volume 5, Issue 1, Pages 55–70, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-006-0058-5, March 2007

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Published Online:


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

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