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Issue 4, 2012
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Is nevirapine atropisomeric? Experimental and computational evidence for rapid conformational inversion

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Abstract

The non-nucleoside reverse transcriptase inhibitor nevirapine displays in its room temperature 1H-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.

Graphical abstract: Is nevirapine atropisomeric? Experimental and computational evidence for rapid conformational inversion

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Supplementary files

Article information


Submitted
30 Aug 2011
Accepted
21 Nov 2011
First published
22 Nov 2011

Org. Biomol. Chem., 2012,10, 716-719
Article type
Communication

Is nevirapine atropisomeric? Experimental and computational evidence for rapid conformational inversion

E. W. D. Burke, G. A. Morris, M. A. Vincent, I. H. Hillier and J. Clayden, Org. Biomol. Chem., 2012, 10, 716
DOI: 10.1039/C1OB06490H

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