TY - JOUR PY - 2008// TI - Cooperative Binding of Calix[4]pyrrole–Anion Complexes and Alkylammonium Cations in Halogenated Solvents JO - Chemistry: a European journal A1 - Gross, Dustin E A1 - Schmidtchen, Franz P A1 - Antonius, Wiebke A1 - Gale, Philip A A1 - Lynch, Vincent M A1 - Sessler, Jonathan L SP - 7822 EP - 7827 VL - 14 IS - 26 N2 - 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.

LA - SN - 0947-6539 UR - http://dx.doi.org/10.1002/chem.200800899 ID - ref1 ER -