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Calix[4]pyrrole as a chloride anion receptor: Solvent and countercation effects

Calix[4]pyrrole as a chloride anion receptor: Solvent and countercation effects
Calix[4]pyrrole as a chloride anion receptor: Solvent and countercation effects
The interaction of calixpyrrole with several chloride salts has been studied in the solid state by X-ray crystallography as well as in solution by isothermal titration calorimetry (ITC) and H-1 NMR spectroscopic titrations. The titration results in dimethylsulfoxide, acetonitrile, nitromethane, 1,2-dichloroethane, and dichloromethane, carried out using various chloride salts, specifically tetraethylammonium (TEA), tetrapropylammonium (TPA), tetrabutylammonium (TBA), tetraethylphosphonium (TEP), tetrabutylphosphonium (TBP), and tetraphenylphosphonium (TPhP), showed no dependence on method of measurement. The resulting affinity constants (K-a), on the other hand, were found to be highly dependent on the choice of solvent with K-a's ranging from 10(2)-10(5) M-1 being recorded in the test solvents used for this study. In dichloromethane, a strong dependence on the countercation was also seen, with the Ka's for the interaction with chloride ranging from 10(2)-10(4) M-1. In the case of TPA, TBA, and TBP, the ITC data could not be fit to a 1:1 binding profile.
isothermal titration calorimetry, selective recognition, statistical error, extended-cavity, binding agents, solid-state, ion-pair, calixpyrrole, complexation, substitution
0002-7863
12281-12288
Sessler, Jonathan L.
d793ea76-a3a2-4ce1-a8d5-aca7d3307fbe
Gross, Dustin E.
7e100882-efc6-4562-902d-f48fdff01d07
Cho, Won-Seob
5e6f841e-5f4b-428d-98dd-49a98efe138c
Lynch, Vincent M.
1ca6d39d-b02d-4141-ab55-f566f00a09b5
Schmidtchen, Franz P.
03556e34-826a-443d-a1b3-2c119f7133bd
Bates, Gareth W.
784ac62e-67f5-400a-ab9a-42615be9ec9d
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Sessler, Jonathan L.
d793ea76-a3a2-4ce1-a8d5-aca7d3307fbe
Gross, Dustin E.
7e100882-efc6-4562-902d-f48fdff01d07
Cho, Won-Seob
5e6f841e-5f4b-428d-98dd-49a98efe138c
Lynch, Vincent M.
1ca6d39d-b02d-4141-ab55-f566f00a09b5
Schmidtchen, Franz P.
03556e34-826a-443d-a1b3-2c119f7133bd
Bates, Gareth W.
784ac62e-67f5-400a-ab9a-42615be9ec9d
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943

Sessler, Jonathan L., Gross, Dustin E., Cho, Won-Seob, Lynch, Vincent M., Schmidtchen, Franz P., Bates, Gareth W., Light, Mark E. and Gale, Philip A. (2006) Calix[4]pyrrole as a chloride anion receptor: Solvent and countercation effects. Journal of the American Chemical Society, 128 (37), 12281-12288. (doi:10.1021/ja064012h).

Record type: Article

Abstract

The interaction of calixpyrrole with several chloride salts has been studied in the solid state by X-ray crystallography as well as in solution by isothermal titration calorimetry (ITC) and H-1 NMR spectroscopic titrations. The titration results in dimethylsulfoxide, acetonitrile, nitromethane, 1,2-dichloroethane, and dichloromethane, carried out using various chloride salts, specifically tetraethylammonium (TEA), tetrapropylammonium (TPA), tetrabutylammonium (TBA), tetraethylphosphonium (TEP), tetrabutylphosphonium (TBP), and tetraphenylphosphonium (TPhP), showed no dependence on method of measurement. The resulting affinity constants (K-a), on the other hand, were found to be highly dependent on the choice of solvent with K-a's ranging from 10(2)-10(5) M-1 being recorded in the test solvents used for this study. In dichloromethane, a strong dependence on the countercation was also seen, with the Ka's for the interaction with chloride ranging from 10(2)-10(4) M-1. In the case of TPA, TBA, and TBP, the ITC data could not be fit to a 1:1 binding profile.

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Published date: 2006
Keywords: isothermal titration calorimetry, selective recognition, statistical error, extended-cavity, binding agents, solid-state, ion-pair, calixpyrrole, complexation, substitution

Identifiers

Local EPrints ID: 44540
URI: http://eprints.soton.ac.uk/id/eprint/44540
ISSN: 0002-7863
PURE UUID: 39f0e673-df49-454b-8113-26f93228b4fa
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: 07 Mar 2007
Last modified: 17 Dec 2019 01:54

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Contributors

Author: Jonathan L. Sessler
Author: Dustin E. Gross
Author: Won-Seob Cho
Author: Vincent M. Lynch
Author: Franz P. Schmidtchen
Author: Gareth W. Bates
Author: Mark E. Light ORCID iD
Author: Philip A. Gale ORCID iD

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