title: Is nevirapine atropisomeric? Experimental and computational evidence for rapid conformational inversion.
abstract: The non-nucleoside reverse transcriptase inhibitor nevirapine displays in its room temperature (1)H-NMR spectrum signals characteristic of a chiral compound. Following suggestions in the recent literature that nevirapine may display atropisomerism-and therefore be a chiral compound, due to slow interconversion between two enantiomeric conformers-we report the results of an NMR and computational study which reveal that while nevirapine does indeed possess two stable enantiomeric conformations, they interconvert with a barrier of about 76 kJ mol(-1) at room temperature. Nevirapine has a half life for enantiomerisation at room temperature of the order of seconds, is not atropisomeric, and cannot exist as separable enantiomers.
authors.affiliation: School of Chemistry, University of Manchester, Manchester, UK.
authors.forename: Edmund W D
authors.initials: EW
authors.lastname: Burke
authors.forename: Gareth A
authors.initials: GA
authors.lastname: Morris
authors.forename: Mark A
authors.initials: MA
authors.lastname: Vincent
authors.forename: Ian H
authors.initials: IH
authors.lastname: Hillier
authors.forename: Jonathan
authors.initials: J
authors.lastname: Clayden
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D019829:Nevirapine / Q000737:chemistry*
chemical_list: D019380:Anti-HIV Agents; D019829:Nevirapine