Intramolecular Motions in 1,2,3-Triethyldiaziridine: A Quantum Chemistry Study
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CTURE OF MATTER AND QUANTUM CHEMISTRY
Intramolecular Motions in 1,2,3-Triethyldiaziridine: A Quantum Chemistry Study L. S. Khaikina,*, G. G. Ageeva, O. E. Grikinaa, I. F. Shishkova, V. V. Kuznetsovb,**, and N. N. Makhovab a Department b
of Chemistry, Moscow State University, Moscow, 119991 Russia
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991 Russia *е-mail: [email protected] **е-mail: [email protected] Received November 11, 2019; revised November 11, 2019; accepted January 21, 2020
Abstract—The potential energy surface of a 1,2,3-triethyldiaziridine molecule is studied with quantum chemical calculations at the B3LYP/cc-pVTZ and MP2/cc-pVTZ levels of theory. A relationship between the energy of a molecular system and the rotation of ethyl groups is considered. It is found that there are 12 configurations that differ slightly in energy, due to different rotation angles of ethyl groups relative to a threemembered ring. The barriers between the minima on the potential energy surface are relatively low. The structural characteristics of different configurations are obtained. Keywords: quantum-chemical calculations, 1,2,3-triethyldiaziridine, potential energy, rotation of ethyl groups DOI: 10.1134/S0036024420090125
INTRODUCTION Derivatives of diaziridine, a saturated three-membered heterocycle with two intracyclic nitrogen atoms, are of great interest from both theoretical and practical points of view [1–4]. They are easily synthesized via the interaction between carbonyl compounds, primary aliphatic amines, and amination reagents. They can also be easily opened under the action of electrophilic reagents, due to the strain of a three-membered cycle, allowing us to obtain different nitrogen-containing heterocyclic compounds [3, 5–11]. A unique property of diaziridines is a rare stable pyramidal configuration of substituents on their nitrogen atoms, so they are convenient objects for studying the stereochemistry of nitrogen organic compounds [4, 12–14]. Diaziridines have low toxicity relative to hydrazine derivatives, making them widely usable. There are now diaziridine derivatives that are promising neurotropic drugs for targeted effects on the central nervous system, and thus different neurotropic activities [15, 16]. Tetramezine in particular, which displays effective antidepressant activity like its more familiar counterparts but has a more rapid therapeutic effect on the central nervous system, was obtained and studied in this series [14, 17, 18]. Diaziridines have high positive enthalpies of formation due to the strain of the three-membered cycle and the presence of N–N intracyclic bonds, so
they are of interest as potential effective combustible components of liquid rocket fuels [19, 20]. Diaziridine derivatives are usually liquid compounds, and their structure cannot be studied by X-ray diffraction. In addition, X-ray diffraction data do not reproduce the structure of a free molecule, since the forces of intermolecular interaction that deform the structure of a single molec
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