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Synthesis and anion binding behaviour of diamide derivatives of pyrrole-2,5-diacetic acid

Synthesis and anion binding behaviour of diamide derivatives of pyrrole-2,5-diacetic acid
Synthesis and anion binding behaviour of diamide derivatives of pyrrole-2,5-diacetic acid
Four examples of bis-amidopyrrole derivatives of pyrrole-2,5-diacetic acid have been prepared. The reaction of diethyl pyrrole-2,5-diacetate with a large excess (24 equiv.) of N,N-dimethylethylenediamine gave N,N0-bis(2-dimethylaminoethyl)-1H-pyrrole-2,5-diacetamide (1). Three further examples, N,N0-bis[2-(2-pyridyl)ethyl]-1H-pyrrole-2,5-diacetamide (2), N,N-bis(2-pyridylmethyl)-1H-pyrrole-2,5-diacetamide (3) and N,N0-dibenzyl-1H-pyrrole-2,5-diacetamide (4), were prepared in a one pot procedure by converting pyrrole-2,5-diacetic acid into the N-hydroxysuccinimide ester and then reacting this with four equivalents of the appropriate amine, 2-(2-aminoethyl)pyridine, 2-aminomethylpyridine or benzylamine, respectively. Compounds 1–4 are shown to be effective anion receptors in acetonitrile-d3 solution, with comparable binding affinities to those found for simple pyrrole-2,5-dicarboxamides, despite possessing a more flexible hydrogen bonding array.
anion binding, pyrrole, supramolecular chemsutry, hydrogen bond
1144-0546
1340-1343
Li, Rongqing
57cf0226-5e02-4ce4-a0e8-84d361585e6c
Evans, Louise S.
c9b34cb4-14cc-4587-a145-abdb0a74ead7
Larsen, David S.
b0f13c30-43dc-4796-a3a8-5a87cbf1a80d
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Brooker, Sally
2ee9681a-3ff7-41be-88c5-681f66b953ef
Li, Rongqing
57cf0226-5e02-4ce4-a0e8-84d361585e6c
Evans, Louise S.
c9b34cb4-14cc-4587-a145-abdb0a74ead7
Larsen, David S.
b0f13c30-43dc-4796-a3a8-5a87cbf1a80d
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Brooker, Sally
2ee9681a-3ff7-41be-88c5-681f66b953ef

Li, Rongqing, Evans, Louise S., Larsen, David S., Gale, Philip A. and Brooker, Sally (2004) Synthesis and anion binding behaviour of diamide derivatives of pyrrole-2,5-diacetic acid. New Journal of Chemistry, 28 (11), 1340-1343. (doi:10.1039/b412654h).

Record type: Article

Abstract

Four examples of bis-amidopyrrole derivatives of pyrrole-2,5-diacetic acid have been prepared. The reaction of diethyl pyrrole-2,5-diacetate with a large excess (24 equiv.) of N,N-dimethylethylenediamine gave N,N0-bis(2-dimethylaminoethyl)-1H-pyrrole-2,5-diacetamide (1). Three further examples, N,N0-bis[2-(2-pyridyl)ethyl]-1H-pyrrole-2,5-diacetamide (2), N,N-bis(2-pyridylmethyl)-1H-pyrrole-2,5-diacetamide (3) and N,N0-dibenzyl-1H-pyrrole-2,5-diacetamide (4), were prepared in a one pot procedure by converting pyrrole-2,5-diacetic acid into the N-hydroxysuccinimide ester and then reacting this with four equivalents of the appropriate amine, 2-(2-aminoethyl)pyridine, 2-aminomethylpyridine or benzylamine, respectively. Compounds 1–4 are shown to be effective anion receptors in acetonitrile-d3 solution, with comparable binding affinities to those found for simple pyrrole-2,5-dicarboxamides, despite possessing a more flexible hydrogen bonding array.

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More information

Published date: 2004
Additional Information: This paper concenrs a joint project between Southampton (Gale group) and the University of Otago in New Zealand (Sally Brooker and co-workers).
Keywords: anion binding, pyrrole, supramolecular chemsutry, hydrogen bond

Identifiers

Local EPrints ID: 15723
URI: http://eprints.soton.ac.uk/id/eprint/15723
ISSN: 1144-0546
PURE UUID: b32e5775-7dd6-4ddd-be27-83b97309f3ab
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

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Date deposited: 24 May 2005
Last modified: 16 Mar 2024 03:16

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Contributors

Author: Rongqing Li
Author: Louise S. Evans
Author: David S. Larsen
Author: Philip A. Gale ORCID iD
Author: Sally Brooker

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