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.
Smrcok
Lubomír
L
Institute of Inorganic Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 36 Bratislava, Slovakia. uachsmrk@savba.sk
Sládkovicová
Mariana
M
Langer
Vratislav
V
Wilson
Chick C
CC
Koós
Miroslav
M
D018360:Crystallography, X-Ray; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D033363:Neutron Diffraction
C014989:1,6-anhydro-beta-glucopyranose; D005947:Glucose