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Quantum-chemical study of organic reaction mechanisms. XI.*1 Biologically active 4-substituted 1,2,4-triazoles from diformylhydrazine and aminophenols

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Abstract

Derivatives of 1,2,4-triazole exhibit antimicrobial, anticonvulsant, anti-inflammatory, immunomodulatory, and other types of activity, which makes it possible to create effective drugs on their basis. Understanding the reaction mechanism for the formation of triazoles helps to control the chemical process and conduct targeted synthesis. Quantum-chemical modeling of the mechanism of interaction of diformylhydrazine with o- and p-aminophenols was carried out using the combined approach CCSD (T)/6–31+G*//B3LYP/6–311++G**. The elementary stages of the reaction, possible intermediate compounds, and transition states have been established. The obtained results have been compared with the data from NMR spectroscopy.

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Data availability

The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Acknowledgements

Optimization of geometric parameters and calculation of molecular energy were performed by the CCSD(T)/6-31+G*//B3LYP/6-311++G** methods using the GAUSSIAN 09 program [22] at A.E. Favorsky Irkutsk Institute of Chemistry SB RAS on the computing cluster of the Baikal Analytical Center for Collective Use of the SB RAS (http://ckp-rf.ru/ckp/3050/). Experimental NMR results were also obtained with use of the equipment of the Baikal Analytical Centre for Collective Use of the SB RAS.

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Authors and Affiliations

  1. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1, Favorsky Str, 664033, Irkutsk, Russia

    Elena Chirkina & Lyudmila Larina

  2. Angarsk State Technical University, 60, Chaikovsky Str, 665835, Angarsk, Irkutsk Region, Russia

    Elena Chirkina

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  1. Elena Chirkina
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  2. Lyudmila Larina
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All authors contributed to the study conception and design. Material preparation, data collection, and analysis were performed by Chirkina Elena and Larina Lyudmila. The first draft of the manuscript was written by Chirkina Elena and Larina Lyudmila commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Elena Chirkina.

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Chirkina, E., Larina, L. Quantum-chemical study of organic reaction mechanisms. XI.*1 Biologically active 4-substituted 1,2,4-triazoles from diformylhydrazine and aminophenols. Struct Chem 33, 2023–2032 (2022). https://doi.org/10.1007/s11224-022-01969-1

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