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An intramolecular bifurcated H-bond from the axial HO-2 group to the axial F-4 atom and to the O5 atom of α-D-hexopyranosides in apolar solvents is evidenced in (1)H NMR spectra. The H-accepting properties of the F atom are modulated by the orientation of the O-substituent at the C3 atom and by an additional F atom at the C4 atom.

Original publication

DOI

10.1002/anie.201303766

Type

Journal article

Journal

Angew Chem Int Ed Engl

Publication Date

27/09/2013

Volume

52

Pages

10524 - 10528

Keywords

carbohydrates, density functional calculations, fluorinated alcohols, hydrogen bonds, scalar couplings, Carbohydrates, Hydrocarbons, Fluorinated, Hydrogen Bonding, Models, Molecular, Molecular Structure, Pyrans