Article Dans Une Revue Organic Letters Année : 2019

Intramolecular OH/π versus C–H/O H-Bond-Dependent Conformational Control about Aryl–C(sp 3 ) Bonds in Cannabidiol Derivatives

Résumé

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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Dates et versions

hal-02892822 , version 1 (07-07-2020)

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Citer

Clément Denhez, Pedro Lameiras, Hatice Berber. Intramolecular OH/π versus C–H/O H-Bond-Dependent Conformational Control about Aryl–C(sp 3 ) Bonds in Cannabidiol Derivatives. Organic Letters, 2019, 21 (17), pp.6855-6859. ⟨10.1021/acs.orglett.9b02484⟩. ⟨hal-02892822⟩
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