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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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Publication details

The article was received on 30 Aug 2011, accepted on 21 Nov 2011 and first published on 22 Nov 2011


Article type: Communication
DOI: 10.1039/C1OB06490H
Citation: Org. Biomol. Chem., 2012,10, 716-719
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    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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