Intramolecular OH/π versus C-H/O H-Bond-Dependent Conformational Control about Aryl-C(sp) Bonds in Cannabidiol Derivatives.
Fiche publication
Date publication
août 2019
Journal
Organic letters
Auteurs
Membres identifiés du Cancéropôle Est :
Dr BERBER Hatice
Tous les auteurs :
Denhez C, Lameiras P, Berber H
Lien Pubmed
Résumé
Conformational control in cannabidiol derivatives has been studied by NMR, XRD, and DFT. The stabilization of their axial and conformations about the aryl-C(sp) 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 conformation. In polar solvents, the CH/O H-bond shifts the equilibrium toward the conformer because of the breaking of the OH/π bond.
Référence
Org. Lett.. 2019 Aug 20;: