1421700-41-5Relevant articles and documents
Light initiated E-Z and Z-E isomerization of isatinphenylsemicarbazones: Tautomeric equilibrium effect
Jakusová, Klaudia,Cigáň, Marek,Donovalová, Jana,Gáplovsky, Martin,Sokolík, Robert,Gáplovsky, Anton
, p. 60 - 69 (2014)
The light and thermally initiated mutual E- and Z-isomer transformations of two efficient isatin N-phenylsemicarbazone colorimetric sensors for strongly basic anions differing in sensitivity, selectivity and sensing mechanism were investigated in solvents
Isatinphenylsemicarbazones as efficient colorimetric sensors for fluoride and acetate anions - Anions induce tautomerism
Jakusová, Klaudia,Donovalová, Jana,Cigáň, Marek,Gáplovsky, Martin,Garaj, Vladimír,Gáplovsky, Anton
, p. 421 - 429 (2014/02/14)
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 1H 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.