Quantum-chemical calculations of the enthalpy of formation for 5/6/5 tricyclic tetrazine derivatives annelated with nitrotriazoles
- Authors: Volokhov V.M.1, Parakhin V.V.2, Amosova E.S.1, Volokhov A.V.1, Lempert D.B.1, Zyubina T.S.1
-
Affiliations:
- Institute of problems of chemical physics Russian academy of sciences
- N.D. Zelinskiy Institute of organic chemistry Russian academy of sciences
- Issue: Vol 43, No 1 (2024)
- Pages: 13-23
- Section: СТРОЕНИЕ ХИМИЧЕСКИХ СОЕДИНЕНИЙ, КВАНТОВАЯ ХИМИЯ, СПЕКТРОСКОПИЯ
- URL: https://cijournal.ru/0207-401X/article/view/674994
- DOI: https://doi.org/10.31857/S0207401X24010026
- EDN: https://elibrary.ru/mlodle
- ID: 674994
Cite item
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.
Full Text

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
References
- P Yin., Q. Zhang, J. M. Shreeve, Acc. Chem. Res. 49, 4 (2016). https://doi.org/10.1021/acs.accounts.5b00477
- Y. Qu, S. P. Babailov, J. Mater. Chem. A. 6, 1915 (2018). https://doi.org/10.1039/C7TA09593
- C. Yongjin, B. Shuhong, Johnson Matthey Technol. Rev. 63, 51 (2019). https://doi.org/10.1595/205651319x15421043166627
- L. L. Fershtat, N. N. Makhova, ChemPlusChem. 85, 12 (2020). https://doi.org/10.1002/cplu.201900542
- H. Gao, Q. Zhang, J. M. Shreeve, J. Mater. Chem. A. 8, 4193 (2020). https://doi.org/10.1039/C9TA12704F
- J. Zhang, J. Zhou, F. Bi, B. Wang, Chin. Chem. Lett. 31, 2375 (2020). https://doi.org/10.1016/j.cclet.2020.01.026
- J. Zhou, J. L. Zhang, B. Z. Wang et al., FirePhysChem. 2, 83 (2022). https://doi.org/10.1016/j.fpc.2021.09.005
- J. Tang, H. Yang, Y. Cui, G. Cheng, Mater. Chem. Front. 5, 7108 (2021). https://doi.org/10.1039/D1QM00916H
- A. M. Churakov, A. A. Voronin, M. S. Klenov, V. A. Tartakovsky, Other Tetrazines and Pentazines in Comprehensive Heterocyclic Chemistry IV, ed. D. S. Black, J. Cossy, C. V. Stevens. Amsterdam: Elsevier Science 9 640 (2022). https://doi.org/10.1016/B978-0-12-818655-8.00064-0
- S. G. Zlotin, I. L. Dalinger, N. N. Makhova, V. A. Tartakovsky, Russ. Chem. Rev. 89, 1 (2020). https://doi.org/ 10.1070/RCR4908
- S. G. Zlotin, A. M. Churakov, M. P. Egorov et al., Mendeleev Commun. 31, 731 (2021). https://doi.org/10.1016/j.mencom.2021.11.001
- A. O. Shvets, A. A. Konnov, M. S. Klenov et al., Russ. Chem. Bull., Int. Ed. 69, 739 (2020). https://doi.org/10.1007/s11172-020-2826-3
- D. A. Gulyaev, M. S. Klenov, A. M. Churakov et al., Russ. Chem. Bull., Int. Ed. 70, 1599 (2021). https://doi.org/10.1007/s11172-021-3256-6
- I. N. Zyuzin, V. M. Volokhov, D. B. Lempert, Russ. J. Phys. Chem. B (Engl. Transl.). 15, 810 (2021). https://doi.org/10.1134/S1990793121050109
- I. N. Zyuzin, I. Yu. Gudkova, D. B. Lempert, Russ. J. Phys. Chem. B (Engl. Transl.). 15, 611 (2021). https://doi.org/10.1134/S1990793121040138
- V. V. Zakharov, N. V. Chukanov, G. V. Shilov, et al., Russ. J. Phys. Chem. B (Engl. Transl.). 15, 622 (2021). https://doi.org/10.1134/S1990793121040126
- L.L. Fershtat // FirePhysChem. (China). 3, 78 (2023). https://doi.org/10.1016/j.foc.2022.09.005
- D. E. Chavez, J. C. Bottaro, M. Petrie, D. A. Parrish, Angew. Chem. Int. Ed. 54, 12973 (2015). https://doi.org/10.1002/anie.201506744
- Y. Tang, D. Kumar, J. M. Shreeve, J. Am. Chem. Soc. 139, 13684 (2017). https://doi.org/10.1021/jacs.7b08789
- Y. X. Tang, C. L. He, P. Yin et al., Eur. J. Org. Chem. 19, 2273 (2018). https://doi.org/10.1002/ejoc.201800347
- G.F. Rudakov et al. // Chem. Eng. J.2022. V. 450. P. 138073; https://doi.org/10.1016/j.cej.2022.138073
- V. M. Volokhov, E. S. Amosova, A. V. Volokhov et al., Comput. Theor. Chem. 1209, 113608 (2022). https://doi.org/10.1016/j.comptc.2022.113608
- L. A. Curtiss, P. C. Redfern, K., J. Raghavachari Chem. Phys. 126, 084108 (2007). https://doi.org/10.1063/1.2436888
- A. Nirwan, V. D. Ghule, Theor. Chem. Acc. 137, 1 (2018). https://doi.org/10.1007/s00214-018-2300-6
- M. A. Suntsova, O. V. Dorofeeva, J. Chem. Eng. Data. 61, 313 (2016). https://doi.org/10.1021/acs.jced.5b00558
- J. Glorian, K. T. Han, S. Braun, B. Baschung, Propellants Explos. Pyrotech. 46, 124 (2021). https://doi.org/10.1002/prep.202000187
- K. K. Irikura, D. J. Frurip, Computational Thermochemistry. ACS Symposium Series 667. Washington: American Chemical Society (1998).
- Parallel Computational Technologies. PCT 2020. Communications in Computer and Information Science, Eds L. Sokolinsky, M. Zymbler. Springer, Cham. 1263, 291 (2020). https://doi.org/10.1007/978-3-030-55326-5_21
- Supercomputing. RuSCDays 2020. Communications in Computer and Information Science, Eds V. Voevodin, S. Sobolev. Springer, Cham. 1331, 310 (2020). https://doi.org/10.1007/978-3-030-64616-5_27
- D. B. Lempert, V. M. Volokhov, I. N. Zyuzin et al., Russ. J. Appl. Chem. (Engl. Transl.). 93, 1852 (2020). https://doi.org/10.1134/S1070427220120071
- V. M. Volokhov, E. S. Amosova, A. V. Volokhov et al., Supercomput. Front. Innov. 7, 68 (2020). https://doi.org/10.14529/jsfi200406
- V. M. Volokhov, T. S. Zyubina, A. V. Volokhov et al., Russ. J. Phys. Chem. B (Engl. Transl.) 15, 12 (2021). https://doi.org/10.1134/S1990793121010127
- V. M. Volokhov, T. S. Zyubina, A. V. Volokhov et al., Russ. J. Inorg. Chem. (Engl. Transl.). 66, 78 (2021).
- https://doi.org/ 10.1134/S0036023621010113
- A. D. Becke, J. Chem. Phys. 98, 5648 (1993). https://doi.org/10.1063/1.464906
- B. J. Johnson, P. M. W. Gill, J. A. Pople, J. Chem. Phys. 98, 5612 (1993). https://doi.org/10.1063/1.464906
- Y. Zhao, D.G. Truhlar, Theor. Chem. Acc. 120, 215 (2008). https://doi.org/10.1007/s00214-007-0310-x
- J.-D. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys. 10, 6615 (2008). https://doi.org/10.1039/B810189B
- L. A. Curtiss, P.C. Redfern, K. Raghavachari, J. Chem. Phys. 127, 124105 (2007). https://doi.org/10.1063/1.2770701
- L. A.Curtiss, P.C.Redfern, K. Raghavachari, Comput. Mol. Sci. 1, 810 (2011). V. 1. P. 810. https://doi.org/10.1002/wcms.59
- J. A. Montgomery Jr., M. J. Frisch, et al., J. Chem. Phys. 112, 6532 (2000). https://doi.org/10.1063/1.481224
- G. A Petersson., D.K. Malick, W.G. Wilson, et al., J. Chem. Phys. 109, 10570 (1998); https://doi.org/10.1063/1.477794
- E. F. Byrd, B. M. Rice, J. Phys. Chem. A. 110, 1005 (2006). https://doi.org/10.1021/jp0536192
- E. F. Byrd, B. M. Rice, J. Phys. Chem. A. 113, 5813 (2009). https://doi.org/10.1021/jp806520b
- V. G. Kiselev, C. F. Goldsmith, J. Phys. Chem. A. 123, 9818 (2019). https://doi.org/10.1021/acs.jpca.9b08356
- A. Karton, J. M. L. Martin, J. Chem. Phys. 136, 124114 (2012). https://doi.org/10.1063/1.3697678
- V. D. Ghule, Comput. Theor. Chem. 992, 92 (2012). https://doi.org/10.1016/j.comptc.2012.05.007
- J. Mann, V. D. Ghule, S. Dharavath, Phys. Chem. A. 127, 6467 (2023). https://doi.org/10.1021/0021-9614(89)90060-8
Supplementary files
