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 NN'-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 I 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.
Original language | English |
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Pages (from-to) | 165-172 |
Number of pages | 8 |
Journal | RUSSIAN CHEMICAL BULLETIN |
Volume | 54 |
Issue number | 1 |
DOIs | |
Publication status | Published - 1 Jan 2005 |
Keywords
- macrocycles
- Schiff bases
- X-ray diffraction analysis
- spectrophotometry
- anion receptors
- density functional theory