Cooperative binding of calix[4]pyrrole-anion complexes and alkylammonium cations in halogenated solvents |
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Authors: | Gross Dustin E Schmidtchen Franz P Antonius Wiebke Gale Philip A Lynch Vincent M Sessler Jonathan L |
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Institution: | Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712, USA. |
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Abstract: | Calix4]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 calix4]pyrrole cavity formed upon chloride anion complexation. In dichloromethane, the affinities of simple meso-octamethylcalix4]pyrrole (1) for methyl-, ethyl-, and n-butylammonium chlorides are on the order of 10(5), 10(4), and 10(2) 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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Keywords: | anions calix[4]pyrrole calorimetry cations ion pairing |
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