New polydentate inacrocyclic ligands of hybrid amine-imine and amide-imine types as artificial anion receptors. Synthesis and study of anion binding

E. A. Katayev, G. D. Pantos, V. M. Lynch, J. L. Sessler, M. D. Reshetova, Y. A. Ustynyuk

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 languageEnglish
Pages (from-to)165-172
Number of pages8
JournalRUSSIAN CHEMICAL BULLETIN
Volume54
Issue number1
DOIs
Publication statusPublished - 1 Jan 2005

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Imines
Amides
Amines
Anions
Ligands
Condensation
Propane
Schiff Bases
Bromides
Titration
Nitrates
X ray diffraction analysis
Density functional theory

Keywords

  • macrocycles
  • Schiff bases
  • X-ray diffraction analysis
  • spectrophotometry
  • anion receptors
  • density functional theory

Cite this

New polydentate inacrocyclic ligands of hybrid amine-imine and amide-imine types as artificial anion receptors. Synthesis and study of anion binding. / Katayev, E. A.; Pantos, G. D.; Lynch, V. M.; Sessler, J. L.; Reshetova, M. D.; Ustynyuk, Y. A.

In: RUSSIAN CHEMICAL BULLETIN, Vol. 54, No. 1, 01.01.2005, p. 165-172.

Research output: Contribution to journalArticle

Katayev, E. A. ; Pantos, G. D. ; Lynch, V. M. ; Sessler, J. L. ; Reshetova, M. D. ; Ustynyuk, Y. A. / New polydentate inacrocyclic ligands of hybrid amine-imine and amide-imine types as artificial anion receptors. Synthesis and study of anion binding. In: RUSSIAN CHEMICAL BULLETIN. 2005 ; Vol. 54, No. 1. pp. 165-172.
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AU - Lynch, V. M.

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AU - Reshetova, M. D.

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N2 - 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.

AB - 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.

KW - macrocycles

KW - Schiff bases

KW - X-ray diffraction analysis

KW - spectrophotometry

KW - anion receptors

KW - density functional theory

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