title: N-Tosylpyrrolidine calix[4]pyrrole: synthesis and ion binding studies.
abstract: The synthesis and preliminary solution phase ion binding properties of the N-tosylpyrrolidine calix[4]pyrrole 2 are reported. This β-octaalkyl-substituted calix[4]pyrrole, the first to be prepared via a direct condensation reaction, was obtained by reacting the 3,4-alkyl-functionalized pyrrole 8 with acetone in the presence of an acid catalyst. On the basis of (1)H NMR spectroscopic analyses and isothermal titration calorimetry, it was concluded that, compared with the parent, β-unsubstituted calix[4]pyrrole (1), compound 2 possesses significantly enhanced binding ability for halide anions in chloroform. Furthermore, 2 proved capable of solubilizing in chloroform solution the otherwise insoluble salts, CsF and CsCl. These effects are ascribed to the interactions between the four tosyl groups present in 2 and the counter cations of the halide anion salts.
authors.affiliation: Department of Chemistry and Biochemistry, 1 University Station-A5300, The University of Texas at Austin, Austin, Texas 78712-0165, USA.
authors.forename: Sung Kuk
authors.initials: SK
authors.lastname: Kim
authors.forename: Dustin E
authors.initials: DE
authors.lastname: Gross
authors.forename: Dong-Gyu
authors.initials: DG
authors.lastname: Cho
authors.forename: Vincent M
authors.initials: VM
authors.lastname: Lynch
authors.forename: Jonathan L
authors.initials: JL
authors.lastname: Sessler
mesh_terms: D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007477:Ions / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011758:Pyrroles / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007477:Ions; C571784:N-tosylpyrrolidine calix(4)pyrrole; D011758:Pyrroles; D011759:Pyrrolidines; D047250:Calixarenes