Crystal Structure, Infrared Spectra and DFT Study of Benzyl 2,3-Anhydro-β-D-Ribopyranoside
Journal article, 2011

The crystal structure of benzyl 2,3-anhydro-β-D-ribopyranoside is orthorhombic, P212121, Z = 4. The pyranose ring adopts the EO conformation distorted considerably to the 5HO 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.



Hydrogen bonding

Benzyl 2

IR vibrational spectra



Eva Scholtzová

Vratislav Langer

Chalmers, Chemical and Biological Engineering, Environmental Inorganic Chemistry

Lubomír Smrcok

Miroslav Koós

Vlasta Sasinková

Jan Hirsch

Journal of Chemical Crystallography

1074-1542 (ISSN) 1572-8854 (eISSN)

Vol. 41 2 167-174


Basic sciences

Subject Categories

Medical Biotechnology (with a focus on Cell Biology (including Stem Cell Biology), Molecular Biology, Microbiology, Biochemistry or Biopharmacy)

Theoretical Chemistry

Organic Chemistry

Areas of Advance

Materials Science

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