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Effect of reactants’ concentration on the ratio and yield of E,Z isomers of isatin-3-(4-phenyl)semicarbazone and N-methylisatin-3-(4-phenyl)semicarbazone

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Abstract

In this work, the effect of inter- and intramolecular interactions of reactants and products, reactants concentration as well as the solvent effect on the ratio of E and Z isomers of isatinphenylsemicarbazones in the reaction mixture is examined. Theoretical calculations proved that Z isomers are more stable than E isomers. Experimental results confirmed the noncovalent intermolecular donor-acceptor interactions of the reactants in the reaction mixture at concentrations above 0.1 mol L−1. The E/Z isomer ratio of isatin-3-(4-phenyl)semicarbazone (I) and N-methylisatin-3-(4-phenyl)semicarbazone (II) depends on the initial concentrations of 3-amino-1-phenylurea (phenylsemicarbazide; V) and 1H-indole-2,3-dione (isatin; III), or 3-methylindol-2,3(1H)-dion (3-methylisatin; IV), respectively. Both isomers exhibit high thermal stability. Thermal E-Z isomerization takes place at temperatures above 70°C in N,N-dimethylformamide.

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Authors and Affiliations

  1. Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, 842 15, Bratislava, Slovakia

    Klaudia Jakusová, Jana Donovalová, Marek Cigáň, Henrieta Stankovičová, Robert Sokolík, Jan Gašpar & Anton Gáplovský

  2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Kalinčiakova 8, 832 32, Bratislava, Slovakia

    Martin Gáplovský

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  1. Klaudia Jakusová
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  2. Martin Gáplovský
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  3. Jana Donovalová
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  4. Marek Cigáň
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Correspondence to Klaudia Jakusová.

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Dedicated to Professor Štefan Toma on the occasion of his 75th birthday

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Jakusová, K., Gáplovský, M., Donovalová, J. et al. Effect of reactants’ concentration on the ratio and yield of E,Z isomers of isatin-3-(4-phenyl)semicarbazone and N-methylisatin-3-(4-phenyl)semicarbazone. Chem. Pap. 67, 117–126 (2013). https://doi.org/10.2478/s11696-012-0248-x

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  • DOI: https://doi.org/10.2478/s11696-012-0248-x

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