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), pp. 3320-3329. (doi:10.1002/chem.200601647).

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Description/Abstract

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)
Keywords: anion binding, molecular recognition, carboxylate, urea, acid, amides, aqueous-solution, thiourea groups, binding, solid-state, neutral anion receptors, host, macrocycles, ureas, complexation
Subjects:
ePrint ID: 54255
Date :
Date Event
2007Published
Date Deposited: 31 Jul 2008
Last Modified: 16 Apr 2017 17:47
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/54255

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