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Isatinphenylsemicarbazones as efficient colorimetric sensors for fluoride and acetate anions - anions induce tautomerism.
Jakusová, Klaudia; Donovalová, Jana; Cigán, Marek; Gáplovský, Martin; Garaj, Vladimír; Gáplovský, Anton.
Afiliación
  • Jakusová K; Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovakia.
  • Donovalová J; Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovakia.
  • Cigán M; Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovakia. Electronic address: cigan@fns.uniba.sk.
  • Gáplovský M; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojárov 10, SK-832 32 Bratislava, Slovakia.
  • Garaj V; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojárov 10, SK-832 32 Bratislava, Slovakia.
  • Gáplovský A; Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK-842 15 Bratislava, Slovakia.
Article en En | MEDLINE | ID: mdl-24418689
ABSTRACT
The anion induced tautomerism of isatin-3-4-phenyl(semicarbazone) derivatives is studied herein. The interaction of F(-), AcO(-), H2PO4(-), Br(-) or HSO4(-) anions with E and Z isomers of isatin-3-4-phenyl(semicarbazone) and N-methylisatin-3-4-phenyl(semicarbazone) as sensors influences the tautomeric equilibrium of these sensors in the liquid phase. This tautomeric equilibrium is affected by (1) the inter- and intra-molecular interactions' modulation of isatinphenylsemicarbazone molecules due to the anion induced change in the solvation shell of receptor molecules and (2) the sensor-anion interaction with the urea hydrogens. The acid-base properties of anions and the difference in sensor structure influence the equilibrium ratio of the individual tautomeric forms. Here, the tautomeric equilibrium changes were indicated by "naked-eye" experiment, UV-VIS spectral and (1)H NMR titration, resulting in confirmation that appropriate selection of experimental conditions leads to a high degree of sensor selectivity for some investigated anions. Sensors' E and Z isomers differ in sensitivity, selectivity and sensing mechanism. Detection of F(-) or CH3COO(-) anions at high weakly basic anions' excess is possible.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Semicarbazonas / Fluoruros / Acetatos Idioma: En Revista: Spectrochim Acta A Mol Biomol Spectrosc Asunto de la revista: BIOLOGIA MOLECULAR Año: 2014 Tipo del documento: Article País de afiliación: Eslovaquia

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Semicarbazonas / Fluoruros / Acetatos Idioma: En Revista: Spectrochim Acta A Mol Biomol Spectrosc Asunto de la revista: BIOLOGIA MOLECULAR Año: 2014 Tipo del documento: Article País de afiliación: Eslovaquia