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Intramolecular OH···FC hydrogen bonding in fluorinated carbohydrates: CHF is a better hydrogen bond acceptor than CF2
Guy T Giuffredi1, Véronique Gouverneur, Bruno Bernet
1Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road OX1 3TA Oxford (UK).
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.
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