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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

  • Klaudia Jakusová EMAIL logo , Martin Gáplovský , Jana Donovalová , Marek Cigáň , Henrieta Stankovičová , Robert Sokolík , Jan Gašpar and Anton Gáplovský
Published/Copyright: September 20, 2012
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Chemical Papers
From the journal Chemical Papers Volume 67 Issue 1

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.

Keywords: isatinphenylsemicarbazones; synthesis of E,Z isomers; concentration and solvent dependence; intermolecular interactions

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Published Online: 2012-9-20
Published in Print: 2013-1-1

© 2012 Institute of Chemistry, Slovak Academy of Sciences

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https://doi.org/10.2478/s11696-012-0248-x
Keywords for this article
isatinphenylsemicarbazones; synthesis of E,Z isomers; concentration and solvent dependence; intermolecular interactions

Articles in the same Issue

  1. Professor Dr. Štefan Toma—excellent scientist and teacher—celebrates his 75th birthday
  2. Palladium-catalysed Claisen rearrangement of 6-allyloxypurines
  3. Applicability of photochemically generated pendant benzoyl peroxides in both “grafting from” and “grafting to” techniques
  4. Spectral characterisation of new organic fluorescent dyes with an alkoxysilane moiety and their utilisation for the labelling of layered silicates
  5. Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones
  6. Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines
  7. Methyltrioxorhenium-catalysed oxidation of secondary amines to nitrones in ionic liquids
  8. Thiophenium-ylides: Synthesis and reactivity
  9. Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks
  10. Novel quercetin derivatives: synthesis and screening for anti-oxidant activity and aldose reductase inhibition
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