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Effect of reactants’ concentration on the ratio and yield ofE,Zisomers of isatin-3-(4-phenyl)semicarbazone andN-methylisatin-3-(4-phenyl)semicarbazone

✍ Scribed by Jakusová, Klaudia; Gáplovský, Martin; Donovalová, Jana; Cigáň, Marek; Stankovičová, Henrieta; Sokolík, Robert; Gašpar, Jan; Gáplovský, Anton

Book ID
119932370
Publisher
Versita
Year
2013
Tongue
English
Weight
280 KB
Volume
67
Category
Article
ISSN
0366-6352

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✦ Synopsis

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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