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Cooperative binding of calix[4]pyrrole-anion complexes and alkylammonium cations in halogenated solvents

Cooperative binding of calix[4]pyrrole-anion complexes and alkylammonium cations in halogenated solvents
Cooperative binding of calix[4]pyrrole-anion complexes and alkylammonium cations in halogenated solvents
Calix[4]pyrrole-chloride interactions are affected not only by the choice of countercation in halogenated solvents, but show a specific dependence on the way in which these cations are bound within the electron rich, bowl-like calix[4]pyrrole cavity formed upon chloride anion complexation.

In dichloromethane, the affinities of simple meso-octamethylcalix[4]pyrrole (1) for methyl-, ethyl-, and n-butylammonium chlorides are on the order of 105, 104, and 102 M-1, respectively, as determined from isothermal titration calorimetry (ITC) analyses. These cation-dependent anion affinity effects, while clearly evident, are less pronounced in other halogenated solvents, such as 1,2-dichloroethane. Support for the proposed cation complexation selectivity is provided by solid state X-ray crystallographic analyses.
anions, calix[4]pyrrole, calorimetry, cations, ion pairing
0947-6539
7822
Gross, Dustin E.
45b8d877-875b-4b6b-a5db-11614730ff9d
Schmidtchen, Franz P.
5dd8ed57-d0be-4039-af66-8bb49ceaea40
Antonius, Wiebke
dc1435ec-59bd-4a5f-b017-2def13d00040
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Lynch, Vincent M.
d5fe3c55-5f9f-40f6-a7a0-988abca91899
Sessler, Jonathan L.
94122c05-9bc9-446a-aecb-6471e6c83d15
Gross, Dustin E.
45b8d877-875b-4b6b-a5db-11614730ff9d
Schmidtchen, Franz P.
5dd8ed57-d0be-4039-af66-8bb49ceaea40
Antonius, Wiebke
dc1435ec-59bd-4a5f-b017-2def13d00040
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Lynch, Vincent M.
d5fe3c55-5f9f-40f6-a7a0-988abca91899
Sessler, Jonathan L.
94122c05-9bc9-446a-aecb-6471e6c83d15

Gross, Dustin E., Schmidtchen, Franz P., Antonius, Wiebke, Gale, Philip A., Lynch, Vincent M. and Sessler, Jonathan L. (2008) Cooperative binding of calix[4]pyrrole-anion complexes and alkylammonium cations in halogenated solvents. Chemistry - A European Journal, 14 (26), 7822. (doi:10.1002/chem.200800899).

Record type: Article

Abstract

Calix[4]pyrrole-chloride interactions are affected not only by the choice of countercation in halogenated solvents, but show a specific dependence on the way in which these cations are bound within the electron rich, bowl-like calix[4]pyrrole cavity formed upon chloride anion complexation.

In dichloromethane, the affinities of simple meso-octamethylcalix[4]pyrrole (1) for methyl-, ethyl-, and n-butylammonium chlorides are on the order of 105, 104, and 102 M-1, respectively, as determined from isothermal titration calorimetry (ITC) analyses. These cation-dependent anion affinity effects, while clearly evident, are less pronounced in other halogenated solvents, such as 1,2-dichloroethane. Support for the proposed cation complexation selectivity is provided by solid state X-ray crystallographic analyses.

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More information

Published date: 21 July 2008
Keywords: anions, calix[4]pyrrole, calorimetry, cations, ion pairing

Identifiers

Local EPrints ID: 144951
URI: http://eprints.soton.ac.uk/id/eprint/144951
ISSN: 0947-6539
PURE UUID: d773bffc-f73c-4d52-b927-47cde824a415
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

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Date deposited: 15 Apr 2010 13:28
Last modified: 03 Dec 2019 01:54

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Contributors

Author: Dustin E. Gross
Author: Franz P. Schmidtchen
Author: Wiebke Antonius
Author: Philip A. Gale ORCID iD
Author: Vincent M. Lynch
Author: Jonathan L. Sessler

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