A Lewis acid-mediated conformational switch

Peter C. Knipe, Hannah Lingard, Ian M. Jones, Sam Thompson, Andrew Hamilton

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)7937-7941
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number40
DOIs
Publication statusPublished - Oct 28 2014

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Knipe, P. C., Lingard, H., Jones, I. M., Thompson, S., & Hamilton, A. (2014). A Lewis acid-mediated conformational switch. Organic and Biomolecular Chemistry, 12(40), 7937-7941. https://doi.org/10.1039/c4ob01556h