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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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Article information


Submitted
23 Jul 2014
Accepted
18 Aug 2014
First published
18 Aug 2014

Org. Biomol. Chem., 2014,12, 7937-7941
Article type
Paper
Author version available

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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