Work

N -Tosylpyrrolidine Calix[4]pyrrole: Synthesis and Ion Binding Studies

Year: 2010

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo101882r

Authors: Sung Kuk Kim, Dustin E. Gross, Dong-Gyu Cho, Vincent M. Lynch, Jonathan L. Sessler

Institutions: The University of Texas at Austin, Inha University, Yonsei University

Language: English

Topic: Supramolecular Chemistry and Complexes

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1915311632, Oligopyrrole-based Anion Binding Agents