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On hydrogen bonding in 1,6-anhydro-beta-D-glucopyranose (levoglucosan): X-ray and neutron diffraction and DFT study.

The geometry of hydrogen bonds in 1,6-anhydro-beta-D-glucopyranose (levoglucosan) is accurately determined by refinement of time-of-flight neutron single-crystal diffraction data. Molecules of levoglucosan are held together by a hydrogen-bond array formed by a combination of strong O-H...O and supporting weaker C-H...O bonds. These are fully and accurately detailed by the neutron diffraction study. The strong hydrogen bonds link molecules in finite chains, with hydroxyl O atoms acting as both donors and acceptors of hydroxyl H atoms. A comparison of molecular and solid-state DFT calculations predicts red shifts of O-H and associated blue shifts of C-H stretching frequencies due to the formation of hydrogen bonds in this system.[1]

References

  1. On hydrogen bonding in 1,6-anhydro-beta-D-glucopyranose (levoglucosan): X-ray and neutron diffraction and DFT study. Smrcok, L., Sládkovicová, M., Langer, V., Wilson, C.C., Koós, M. Acta Crystallogr., B (2006) [Pubmed]
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