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Issue 40, 2014
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A Lewis acid-mediated conformational switch

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Abstract

Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis and conformational behaviour of an isonicotinamide-substituted diphenylacetylene upon recognition of Lewis acids, including metalloporphyrins. Binding of these at a remote site – the pyridyl nitrogen – increases hydrogen-bond donor ability of the proximal amide NH, causing an increased preference for the alkyne rotamer in which this hydrogen bond is maintained.

Graphical abstract: A Lewis acid-mediated conformational switch

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Publication details

The article was received on 23 Jul 2014, accepted on 18 Aug 2014 and first published on 18 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01556H
Citation: Org. Biomol. Chem., 2014,12, 7937-7941
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    A Lewis acid-mediated conformational switch

    P. C. Knipe, H. Lingard, I. M. Jones, S. Thompson and A. D. Hamilton, Org. Biomol. Chem., 2014, 12, 7937
    DOI: 10.1039/C4OB01556H

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