Heterocycles p. 285 - 297 (2005)
Update date:2022-08-04
Topics: NMR spectroscopy X-ray crystallography Spectroscopy UV-Visible Spectroscopy Binding assay Alkali Metal Ions Allosteric binding Pseudocryptand C-pivot tripodal ligand 3-hydroxy-2(1H)-pyridinone Ga(III)
Katoh, Akira
Kudo, Hidenori
Saito, Ryota
A novel C-pivot tripodal hexadentate ligand (3,2-HOPOHL) composed of 3-hydroxy-2(1H)-pyridinone as a bidentate ligand, the ethyleneoxy chain as a spacer, and tris(carboxyric acid) as an anchor was synthesized. 3,2-HOPOHL recognized only Na+ ion, suggesting that it pre-organized a cavity due to the electrostatic interaction among the 2(1H)-pyridinone rings. UV-VIS spectroscopic analysis indicated that 3,2-HOPOHL formed a stable intramolecular 1:1 Fe(III) complex in aqueous solution. The stability constant (log K) of 3,2-HOPOHL-Fe(III) complex was estimated to be 27.6 from the competitive reaction with EDTA. 1H-NMR titration of 3,2-HOPOHL-Ga(III) complex with Na+ and K+ ions in CDCl3-CD3CN indicated the formation of 1:1 complexes. The binding constants of Na+- and K+-3,2-HOPOHL-Ga(III) complexes were estimated to be 3.3×103 and 7.8×103 M-1, respectively, the ion selectivity of K+ toward Na+ being more than two-fold.
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