title: Intramolecular OH···FC hydrogen bonding in fluorinated carbohydrates: CHF is a better hydrogen bond acceptor than CF2.
abstract: 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.
authors: Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road OX1 3TA Oxford (UK).
authors: Guy T
authors: GT
authors: Giuffredi
authors: Véronique
authors: V
authors: Gouverneur
authors: Bruno
authors: B
authors: Bernet
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D006845:Hydrocarbons, Fluorinated; D011714:Pyrans
keywords: carbohydrates; density functional calculations; fluorinated alcohols; hydrogen bonds; scalar couplings