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Issue 7, 2014
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Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors

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Abstract

Anion binding studies of 1,10-phenanthroline- and 2-pyridyl-substituted urea-based receptors reveal that guest-dependent conformations exist in structural variants related to a previously investigated bipyridyl-based receptor. Dynamic conformational switching persists in a monofunctional pyridyl-urea receptor, and the preorganization provided by a phenanthroline-based analogue promotes convergence of anion coordinating groups to a single guest. Despite this predisposition for anion coordination, the conformational flexibility of the bipyridyl-based receptor provides the most selective motif for H2PO4 coordination. Furthermore, the two new phenanthrolyl- and pyridyl-receptors serve as models of the bipyridyl-based receptor, elucidating accurate stepwise association constants for 1 : 2 host/guest binding by this receptor, and suggest that oxoanions prefer the embrace of a “U” conformation in 1 : 1 complexes.

Graphical abstract: Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors

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Publication details

The article was received on 01 Apr 2014, accepted on 24 Apr 2014 and first published on 24 Apr 2014


Article type: Edge Article
DOI: 10.1039/C4SC00950A
Citation: Chem. Sci., 2014,5, 2899-2905
  • Open access: Creative Commons BY-NC license
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    Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors

    J. V. Gavette, C. J. Evoniuk, L. N. Zakharov, M. E. Carnes, M. M. Haley and D. W. Johnson, Chem. Sci., 2014, 5, 2899
    DOI: 10.1039/C4SC00950A

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