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Journal of Chemical Crystallography

, Volume 41, Issue 2, pp 167–174 | Cite as

Crystal Structure, Infrared Spectra and DFT Study of Benzyl 2,3-Anhydro-β-d-Ribopyranoside

  • Eva ScholtzováEmail author
  • Vratislav Langer
  • Ľubomír Smrčok
  • Miroslav Koóš
  • Vlasta Sasinková
  • Ján Hirsch
ORIGINAL PAPER
  • 187 Downloads

Abstract

The crystal structure of benzyl 2,3-anhydro-β-d-ribopyranoside is orthorhombic, P212121, Z = 4. The pyranose ring adopts the E O conformation distorted considerably to the 5 H O direction. The molecules of the title compound are linked into infinite chains running along the a-axis by bifurcated O–H···O hydrogen bonds. Interaction energies of these hydrogen bonds are significantly different, ~−5.4 for the bond with the smaller and ~−1.1 kcal/mol for the bond with the larger O···O separation. The hydrogen-bond pattern is completed by the two weaker C–H···O intermolecular hydrogen bonds, aiming at the epoxy oxygen atom. IR vibrational spectrum was interpreted by means of comparison with the full list of vibrational modes predicted using DFT method in the solid state. While till 1495 cm−1 the individual bands can be reconciled with single calculated modes, the region below this limit is populated by heavily overlapped HCH, HCO, HOC, COC and HCC bending modes merged with few ν(CC) and ν(CO) modes. The respective “red” shifts of the positions of the ν(OH) bands correlate well with the size of the O···O separation.

Graphical Abstract

The crystal structure and the analysis of electronic structure and vibrational modes of an important precursor for preparation of model branched oligosaccharides related to xylan, arabinoxylan and 4-O-methylglucuronoxylan have been established and discussed.

Keywords

Benzyl 2,3-anhydro-β-d-ribopyranoside DFT Hydrogen bonding IR vibrational spectra 

Notes

Acknowledgments

This study was partially supported by the Slovak Grant Agency VEGA under the contracts 2/0150/09 and 2/0128/08 and by the Slovak Research and Development Agency (contract no. APVV-0366-07).

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Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Eva Scholtzová
    • 1
    Email author
  • Vratislav Langer
    • 2
  • Ľubomír Smrčok
    • 1
  • Miroslav Koóš
    • 3
  • Vlasta Sasinková
    • 3
  • Ján Hirsch
    • 3
  1. 1.Institute of Inorganic Chemistry, Slovak Academy of SciencesBratislavaSlovakia
  2. 2.Department of Chemical and Biological Engineering, Environmental Inorganic ChemistryChalmers University of TechnologyGothenburgSweden
  3. 3.Institute of Chemistry, Center of Excellence, Slovak Academy of SciencesBratislavaSlovakia

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