New polydentate macrocyclic ligands of hybrid amine-imine and amide-imine types as artificial anion receptors. Synthesis and study of anion binding |
| |
Authors: | E. A. Katayev G. D. Pantos V. M. Lynch J. L. Sessler M. D. Reshetova Yu. A. Ustynyuk |
| |
Affiliation: | (1) Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119992 Moscow, Russian Federation;(2) Department of Chemistry and Biochemistry and Institute for Cellular and Molecular Biology, University of Texas at Austin, 1 University Station, A5300, Austin, Texas 78712 0165, USA |
| |
Abstract: | Three new macrocyclic Schiff bases containing an amine or amide structural fragment along with imine groups were synthesized by condensation of 2,6-bis(2-aminophenyliminomethyl)pyridine (1) and N, N’-bis(2-aminophenyl)pyridine-2,6-dicarboxamide (2) with 2,5-diformylpyrrole (3) and 2,2-bis(5-formylpyrrol-2-yl)propane (4). The reaction of compound 1 with 3 proceeds abnormally and is accompanied by redox disproportionation of compound 1 in the first step. The structure of the macrocyclic product of this reaction was established by X-ray diffraction analysis. Spectrophotometric titration showed that hybrid macrocycle 10, which was prepared by condensation of compound 2 with 4, possesses the properties of an anion receptor and selectively binds hydrosulfate and dihydrophosphate anions in the presence of bromide and nitrate anions. The structures of 10 and its adduct with the hydrosulfate anion were calculated by density functional theory.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 161–168, January, 2005. |
| |
Keywords: | macrocycles Schiff bases X-ray diffraction analysis spectrophotometry anion receptors density functional theory |
本文献已被 SpringerLink 等数据库收录! |
|