Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 4, Pages 716-719Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06490h
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Funding
- Alzeim Ltd.
- EPSRC
- Boehringer Ingelheim (Canada) Ltd
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The non-nucleoside reverse transcriptase inhibitor nevirapine displays in its room temperature H-1-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.
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