Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 26, Pages 7822-7827Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800899
Keywords
anions; calix[4]pyrrole; calorimetry; cations; ion pairing
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Funding
- National Institutes of Health [GM 058907]
- Deutsche Forschungsgemeinschaft [Schm 369/22-1/2]
- Hans-Fischer-Gesellschaft, Munich
- EPSRC
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM058907] Funding Source: NIH RePORTER
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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 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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