Quantum-chemical calculations of the enthalpy of formation for 5/6/5 tricyclic tetrazine derivatives annelated with nitrotriazoles

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Abstract

The paper presents the study of the calculated physicochemical properties of new high-energy 5/6/5 tricyclic structures, which are 1,2,3,4- or 1,2,4,5-tetrazines, fused with a pair of 1H-1,2,4-, 4H-1,2,4- or 1H-1,2,3-triazoles. Values of the enthalpy of formation in the gaseous phase have been determined by high-performance quantum-chemical calculations (within Gaussian 09 program package) using various methods for solving the stationary Schrödinger equation, including G4, G4MP2, ωB97XD/aug-cc-pVTZ, CBS-APNO, CBS-QB3, CBS-4M, B3LYP/6-311+G(2d,p), M062X/6-311+G(2d,p). The results of calculations obtained by the methods of atomization and isogyric reactions have been analysed. Various calculation methods have been compared in terms of accuracy and time consumption.

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About the authors

V. M. Volokhov

Institute of problems of chemical physics Russian academy of sciences

Author for correspondence.
Email: aes@icp.ac.ru
Russian Federation, Chernogolovka

V. V. Parakhin

N.D. Zelinskiy Institute of organic chemistry Russian academy of sciences

Email: aes@icp.ac.ru
Russian Federation, Moscow

E. S. Amosova

Institute of problems of chemical physics Russian academy of sciences

Email: aes@icp.ac.ru
Russian Federation, Chernogolovka

A. V. Volokhov

Institute of problems of chemical physics Russian academy of sciences

Email: aes@icp.ac.ru
Russian Federation, Chernogolovka

D. B. Lempert

Institute of problems of chemical physics Russian academy of sciences

Email: aes@icp.ac.ru
Russian Federation, Chernogolovka

T. S. Zyubina

Institute of problems of chemical physics Russian academy of sciences

Email: aes@icp.ac.ru
Russian Federation, Chernogolovka

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Supplementary files

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2. Fig. 1. Bis(triazolo)tetrazine molecules under study.

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3. Fig. 2. Structures of isomers of the general formula C4N10O4 1a,b–3a,b (from different angles) and their geometric parameters: bond lengths and bond angles (Å, °). Calculations were performed using the B3LYP/6-311+G(2d,p) method.

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4. Fig. 3. Change in the enthalpy of formation in the gas phase (kJ/mol) in the series of studied isomers 1a,b–3a,b. Calculation method B3LYP/6-311+G(2d,p) - 1, M062X/6-311+G(2d,p) - 2, G4MP2 - 3, G4 - 4, CBS-APNO - 5, CBS-QB3 - 6, ωB97XD/aug-cc-pVTZ - 7, CBS-4M - 8.

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5. Fig. 4. IR spectra (e is the molar extinction coefficient) of absorption of isomeric structures 1a,b–3a,b.

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6. Fig. 5. Vectors of atomic displacements for the indicated frequencies (numbers in the figures) of the most intense vibrations of isomeric structures 1a,b–3a,b.

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