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Intramolecular OH/π versus C-H/O H-Bond-Dependent Conformational Control about Aryl-C(sp3) Bonds in Cannabidiol
Clément Denhez1,2, Pedro Lameiras1, Hatice Berber1
1Université de Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, France.
Abstract:
Conformational control in cannabidiol derivatives has been studied by NMR, XRD, and DFT. The stabilization of their axial M and P conformations about the aryl-C(sp3) bond is an effect of competing intramolecular OH/π and CH/O H-bonds. In a nonpolar solvent and in the solid state, the OH/π bond is a determinant of the M conformation. In polar solvents, the CH/O H-bond shifts the equilibrium toward the P conformer because of the breaking of the OH/π bond.
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