DOI: https://doi.org/10.15421/081804

STUDYING THE KINETICS OF LIQUID PHASE HYDRAZINOLYSIS BUTYL 2-(2R-9-OXOACRIDINE-10(9H)-YL)ACETATES

Yuriy V. Karpenko, Ludmila A. Omelyanchyk

Abstract


Synthesis, the study of chemical, physical and biological properties, as well as the practical value of the new derivatives of acridine-9(10H)–one is one of the promising directions in the chemistry of heterocyclic compounds. The study concerns the synthesis of hydrazides of 2-(2R-9-oxoacridine-10(9H)-yl)ethanoic acids, which due to their reactivity are widely used for the synthesis of various nitrogen-containing heterocyclic systems, such as: 1,3,4‑oxadiazole, 1,2,4-triazole and 1,3,4-thiadiazole. The substituted organic hydrazides of 2-(2R-9-oxoacridine-10(9H)-yl)ethanoic acids are widely used in organic and bioorganic chemistry. In this work, the kinetics of the liquid-phase hydrazinolysis of butyl 2-(2R-9-oxoacridine-10(9H)-yl)ethanoates was studied. At the beginning of the study, the thermodynamic characteristics of the reaction and the activation energy were theoretically calculated using GAMESS program. It was found that the activation energy for the formation of 2-(9-oxoacridine-10(9H)-yl)acetohydrazide is 60.47 kJ/mol, and for 2-(2-methyl-9-oxoacridine-10(9H)-yl)acetohydrazide it is 27.09 kJ/mol. Consequently, the reaction of hydrazine with butyl 2-(2-methyl-9-oxoacridine-10(9H)-yl)ethonoate occurs 2.2 times faster than butyl 2-(9-oxoacridine-10(9H)-yl)ethanoate. Subsequently, the kinetics of the reaction of liquid-phase hydrazinolysis was experimentally investigated by the consumption of hydrazine-hydrate in the reaction for the confirmation of theoretical calculations. In the temperature range of 298–343 K the activation energy of the process found from Arrhenius dependence is 15.78 and 7.24 kJ/mol. It is shown that the reaction has a second order of bimolecular substitution. There is proposed a mechanism of the process on the basis of kinetic data.


Keywords


butyl ester; hydrazine-hydrate; kinetics; mechanism; procedure of reaction; GAMESS program

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