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A Lewis acid-mediated conformational switch

A Lewis acid-mediated conformational switch
A Lewis acid-mediated conformational switch
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.
1477-0520
7937-7941
Knipe, Peter C.
a75b6ed7-4d9b-45fc-aacc-49e9e0d0b266
Lingard, Hannah
cbd418c5-5067-4649-aec0-df2520e2146e
Jones, Ian M.
3d141d56-9e92-4ebc-bd47-c248d83dac66
Thompson, Sam
99b7e34e-fe24-401c-b7b0-64e56cbbbcb1
Hamilton, Andrew D.
048a6c75-91bf-4555-ab12-ce885eee65dd
Knipe, Peter C.
a75b6ed7-4d9b-45fc-aacc-49e9e0d0b266
Lingard, Hannah
cbd418c5-5067-4649-aec0-df2520e2146e
Jones, Ian M.
3d141d56-9e92-4ebc-bd47-c248d83dac66
Thompson, Sam
99b7e34e-fe24-401c-b7b0-64e56cbbbcb1
Hamilton, Andrew D.
048a6c75-91bf-4555-ab12-ce885eee65dd

Knipe, Peter C., Lingard, Hannah, Jones, Ian M., Thompson, Sam and Hamilton, Andrew D. (2014) A Lewis acid-mediated conformational switch. Organic & Biomolecular Chemistry, 12 (40), 7937-7941. (doi:10.1039/C4OB01556H).

Record type: Article

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.

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Published date: 18 August 2014
Organisations: Chemistry

Identifiers

Local EPrints ID: 403578
URI: http://eprints.soton.ac.uk/id/eprint/403578
ISSN: 1477-0520
PURE UUID: 59ce1d42-792c-4565-9156-1ec2409b80f4
ORCID for Sam Thompson: ORCID iD orcid.org/0000-0001-6267-5693

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Date deposited: 06 Dec 2016 11:35
Last modified: 03 Dec 2019 01:32

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Contributors

Author: Peter C. Knipe
Author: Hannah Lingard
Author: Ian M. Jones
Author: Sam Thompson ORCID iD
Author: Andrew D. Hamilton

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