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Crystallographic and solution anion binding studies of bis-amidofurans and thiophenes

Crystallographic and solution anion binding studies of bis-amidofurans and thiophenes
Crystallographic and solution anion binding studies of bis-amidofurans and thiophenes
A variety of furan and thiophene amide and thioamide cleft type anion receptors have been synthesised and crystallographically characterised. Unlike 2,5-diamidopyrrole anions, analogous 2,5-diamidofurans and thiophenes do not interlock in the solid state. The anion binding properties of these receptors have been investigated in DMSO/0.5% water solution using H-1 NMR titration techniques. Solution studies and solid-state evidence suggests that the thiophene receptors may utilise a thiophene CH hydrogen atom for hydrogen bond formation to anions with a 2,4-diamidothiophene showing similar anion binding affinities to a 2,5-diamidopyrrole.
anion receptors, amides, thiophene, furan, hydrogen bonds solid-state, ion-pair, receptor, recognition, versatile
1061-0278
469-486
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Warriner, Colin N.
2cdda67a-3408-4a5e-963c-8b0ee7555980
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Warriner, Colin N.
2cdda67a-3408-4a5e-963c-8b0ee7555980

Coles, Simon J., Gale, Philip A., Hursthouse, Michael B., Light, Mark E. and Warriner, Colin N. (2004) Crystallographic and solution anion binding studies of bis-amidofurans and thiophenes. Supramolecular Chemistry, 16 (7), 469-486. (doi:10.1080/10610270410001713303).

Record type: Article

Abstract

A variety of furan and thiophene amide and thioamide cleft type anion receptors have been synthesised and crystallographically characterised. Unlike 2,5-diamidopyrrole anions, analogous 2,5-diamidofurans and thiophenes do not interlock in the solid state. The anion binding properties of these receptors have been investigated in DMSO/0.5% water solution using H-1 NMR titration techniques. Solution studies and solid-state evidence suggests that the thiophene receptors may utilise a thiophene CH hydrogen atom for hydrogen bond formation to anions with a 2,4-diamidothiophene showing similar anion binding affinities to a 2,5-diamidopyrrole.

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More information

Published date: October 2004
Keywords: anion receptors, amides, thiophene, furan, hydrogen bonds solid-state, ion-pair, receptor, recognition, versatile

Identifiers

Local EPrints ID: 20765
URI: http://eprints.soton.ac.uk/id/eprint/20765
ISSN: 1061-0278
PURE UUID: 31d0ea80-6325-4a84-b06b-0c9fa6afc324
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 02 Mar 2006
Last modified: 18 Feb 2021 16:55

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Contributors

Author: Simon J. Coles ORCID iD
Author: Philip A. Gale ORCID iD
Author: Mark E. Light ORCID iD
Author: Colin N. Warriner

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