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Bis(amidopyridine)-linked calix 4 arenes: a novel type of receptor for dicarboxylic acids

Bis(amidopyridine)-linked calix 4 arenes: a novel type of receptor for dicarboxylic acids
Bis(amidopyridine)-linked calix 4 arenes: a novel type of receptor for dicarboxylic acids
Calix[4]arenes 1 and 2, functionalised on their upper rim with amidopyridine groups, have been synthesised. In the case of 1, a detailed binding study with a range of aliphatic and aromatic dicarboxylic acids has been carried out using H-1 NMR spectroscopy. The binding affinities are largely dependent upon the length of the alkyl spacer group, with the highest binding constant observed for dodecanedioic acid. The X-ray crystal structures of 1 and 2 reveal chain structures formed through intermolecular hydrogen bonds between amidopyridine moieties.
calix[4]arene, hydrogen bonding, host guest chemistry, self-organization molecular scaffolds, derivatives, recognition
0040-4039
873-878
Miyaji, H.
d415729c-c2b0-4db2-9057-ad2d72fed11c
Dudic, M.
5f1a61b0-bc8d-46a7-a90e-a0068cee4611
Tucker, J. H. R.
07d2c080-2e71-4fcf-89d6-8dd764345dcc
Prokes, I.
c6565182-4ab9-43e0-b8cf-296507d0f4b8
Light, M. E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Stibor, I.
c58288b5-b0da-4b1e-8d62-e3a88e2288da
Lhotak, P.
c08c7c4f-863e-40dd-9087-37b1794d4fed
Miyaji, H.
d415729c-c2b0-4db2-9057-ad2d72fed11c
Dudic, M.
5f1a61b0-bc8d-46a7-a90e-a0068cee4611
Tucker, J. H. R.
07d2c080-2e71-4fcf-89d6-8dd764345dcc
Prokes, I.
c6565182-4ab9-43e0-b8cf-296507d0f4b8
Light, M. E.
cf57314e-6856-491b-a8d2-2dffc452e161
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Stibor, I.
c58288b5-b0da-4b1e-8d62-e3a88e2288da
Lhotak, P.
c08c7c4f-863e-40dd-9087-37b1794d4fed

Miyaji, H., Dudic, M., Tucker, J. H. R., Prokes, I., Light, M. E., Hursthouse, M. B., Stibor, I. and Lhotak, P. (2002) Bis(amidopyridine)-linked calix 4 arenes: a novel type of receptor for dicarboxylic acids. Tetrahedron Letters, 43 (5), 873-878. (doi:10.1016/S0040-4039(01)02179-7).

Record type: Article

Abstract

Calix[4]arenes 1 and 2, functionalised on their upper rim with amidopyridine groups, have been synthesised. In the case of 1, a detailed binding study with a range of aliphatic and aromatic dicarboxylic acids has been carried out using H-1 NMR spectroscopy. The binding affinities are largely dependent upon the length of the alkyl spacer group, with the highest binding constant observed for dodecanedioic acid. The X-ray crystal structures of 1 and 2 reveal chain structures formed through intermolecular hydrogen bonds between amidopyridine moieties.

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More information

Published date: 28 January 2002
Keywords: calix[4]arene, hydrogen bonding, host guest chemistry, self-organization molecular scaffolds, derivatives, recognition

Identifiers

Local EPrints ID: 19820
URI: http://eprints.soton.ac.uk/id/eprint/19820
ISSN: 0040-4039
PURE UUID: 80155461-ebf9-45f1-a7c9-5c282c2d3921
ORCID for M. E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 17 Feb 2006
Last modified: 09 Jan 2022 02:59

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Contributors

Author: H. Miyaji
Author: M. Dudic
Author: J. H. R. Tucker
Author: I. Prokes
Author: M. E. Light ORCID iD
Author: I. Stibor
Author: P. Lhotak

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