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

Conformational control of selectivity and stability in hybrid amide/urea macrocycles
Conformational control of selectivity and stability in hybrid amide/urea macrocycles
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.
anion binding, molecular recognition, carboxylate, urea, acid, amides, aqueous-solution, thiourea groups, binding, solid-state, neutral anion receptors, host, macrocycles, ureas, complexation
0947-6539
3320-3329
Brooks, Simon J.
fcf66c9a-5e4d-47cf-bc9f-e7c8886a061a
García-Garrido, Sergio E.
339a1aae-f68b-42a8-b807-709e818a99d3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Cole, Pamela A.
a321471f-2d39-4799-8a3e-fdaa29c385e5
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Brooks, Simon J.
fcf66c9a-5e4d-47cf-bc9f-e7c8886a061a
García-Garrido, Sergio E.
339a1aae-f68b-42a8-b807-709e818a99d3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Cole, Pamela A.
a321471f-2d39-4799-8a3e-fdaa29c385e5
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943

Brooks, Simon J., García-Garrido, Sergio E., Light, Mark E., Cole, Pamela A. and Gale, Philip 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).

Record type: Article

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.

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More information

Published date: 2007
Keywords: anion binding, molecular recognition, carboxylate, urea, acid, amides, aqueous-solution, thiourea groups, binding, solid-state, neutral anion receptors, host, macrocycles, ureas, complexation
Organisations: Chemistry

Identifiers

Local EPrints ID: 44231
URI: https://eprints.soton.ac.uk/id/eprint/44231
ISSN: 0947-6539
PURE UUID: d1ea0f4f-a1ad-4606-8dd9-cbfc46a60e86
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

Catalogue record

Date deposited: 20 Feb 2007
Last modified: 14 Mar 2019 01:48

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