Conformational control of selectivity and stability in hybrid amide/urea macrocycles

Brooks, S.L., Garcia-Garrido, S.E., Light, M.E., Cole, P.A. and Gale, P.A. (2007) Conformational control of selectivity and stability in hybrid amide/urea macrocycles. Chemistry-a European Journal, 13, (12), 3320-3329. (doi:10.1002/chem.200601647).


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The anion-binding properties of two similar hybrid amide/urea macrocycles containing either a 2,6-dicarboxamidophenyl or a 2,6-dicarboxamidopyridine group are compared. Significant differences in anion affinity and mode of interaction with anions are attributed to the presence of intramolecular hydrogen bonds in the pyridine system. In fact, remarkably, the phenyl macrocycle undergoes amide hydrolysis under neutral conditions in DMSO/water. The anion binding abilities of the receptors are compared to those of acyclic analogues of the macrocycles that show that the phenyl receptor behaves in a similar fashion to acyclic urea-containing receptors (i.e., showing little selectivity amongst oxo anions), whilst the pyridine-containing receptor shows a high affinity and selectivity for carboxylates.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1002/chem.200601647
ISSNs: 0947-6539 (print)
Related URLs:
Keywords: anion binding, molecular recognition, carboxylate, urea, acid, ,amides, aqueous-solution, thiourea groups, binding, solid-state, neutral anion receptors, host, macrocycles, ureas, complexation
Subjects: Q Science
Q Science > QD Chemistry
Divisions : University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 54255
Accepted Date and Publication Date:
Date Deposited: 31 Jul 2008
Last Modified: 31 Mar 2016 12:33

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