Verification of the mechanisms of thermal transformations of 1,1-diamino-2,2-dinitroethylene (DADNE) based on quantum chemical calculations, thermal analysis and mass spectroscopy of gaseous products

References

• Bellamy, A. J. 2007. FOX-7 (1,1-diamino-2,2-dinitroethene). In High energy density materials, 125: 1–33. T. M. Klapötke (Vol. Ed.), D. M. P. Mingos (Series Ed.), in Structure and Bonding. Berlin: Springer. doi:10.1007/430_2006_054.
   Google Scholar
• Bennion, J. C., N. Chowdhury, J. W. Kampf, and A. J. Matzger. 2016. Hydrogen peroxide solvates of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane. Angewandte Chemie International Edition 55 (42):13118–21. doi:10.1002/anie.201607130.
   PubMed Web of Science ®Google Scholar
• Burnham, A. K., R. K. Weese, R. Wang, Q. S. M. Kwok, and D. E. G. Jones. 2005. Thermal properties of FOX-7. Proc. 36th Int. Annual Conference of ICT 150/1, Karlsruhe, Germany.
   Google Scholar
• Crawford, M.-J., E. M. Jü, T. M. Gobel, K. P. Mayer, G. Oehlinger, and J. M. Welch. 2007. γ-FOX-7: Structure of a high energy density material immediately prior to decomposition. Propellants, Explosives, Pyrotechnics 32:478–95. doi:10.1002/prep.200700240.
   Web of Science ®Google Scholar
• Dorsett, H. 2000. Computational studies of FOX-7, A new insensitive explosive, DSTO-TR-1054, Australian government department of defense. Melbourne, Australia.
   Google Scholar
• Fan, X.-Z., L. Ji-zhen, and Z.-R. Liu. 2007. Thermal Behavior of 1,1-Diamino-2,2-dinitroethylene. The Journal of Physical Chemistry A 111:13291–95. doi:10.1021/jp075889l.
   PubMed Web of Science ®Google Scholar
• Frisch, M. J., G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox. 2009. Gaussian 09. Revision C.01. Gaussian. Inc.: Wallingford CT.
   Google Scholar
• Garmasheva, N. V., I. V. Chemagina, V. P. Filin, M. B. Kazakova, Y. A. Shakhtorin, N. P. Taybinov, V. M. Lagutina, and B. G. Loboiko. 2005. Research of Thermal Decomposition of Diamminodinitroethylene (FOX-7). Proc. 36th Int. Annual Conference of ICT 87/1, Karlsruhe, Germany.
   Google Scholar
• Gies, H. 1983. Studies on clathrasils. III. Crystal structure of melanophlogite, a natural clathrate compound of silica. Z Kristallogr 164:247–57. doi:10.1524/zkri.1983.164.3-4.247.
   Google Scholar
• Gindulyte, A., L. Massa, L. Huang, and J. Karle. 1999. Proposed mechanism of 1,1-Diamino-Dinitroethylene decomposition: A density functional theory study. The Journal of Physical Chemistry A 103:11045–51. doi:10.1021/jp991794a.
   Web of Science ®Google Scholar
• Golovina, N. I., A. V. Raevskiy, N. V. Chukanov, B. L. Korsunskiy, G. V. Shilov, L. O. Atovmyan, and S. M. Aldoshin. 2008. Density of crystals of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane, a potential ligand. Rossiiskiy Khimicheskiy Zhurnal (Russian Chem. J.) 48 (1):41–48. (in Russian).
   Google Scholar
• Ignatov, S. K. Moltran - program for visualization of molecular data and calculations of thermodynamic parameters. N.I. Lobachevsky Nizhny Novgorod State University, http://qchem.unn.ru/moltran,http://github.com/skignatov/moltran [accessed February 3, 2020].
   Google Scholar
• Kempa, P. B., and M. Herrmann. 2005. Temperature resolved X-ray diffraction for the investigation of the phase transitions of FOX-7. Particle & Particle Systems Characterization 22:418–22. doi:10.1002/ppsc.200501006.
   Web of Science ®Google Scholar
• Kiselev, V. G., and N. P. Gritsan. 2014. Unexpected primary reactions for thermolysis of 1,1-Diamino-2,2-dinitroethylene (FOX-7) revealed by ab initio calculations. The Journal of Physical Chemistry A 118:8002–08. doi:10.1021/jp507102x.
   PubMed Web of Science ®Google Scholar
• Krisyuk, B. E., and T. M. Sypko. 2021a. Alternative mechanism of thermolysis of diaminodinitroethylene (FOX-7). Chemical Bulletin 70 (2):424–26. doi:10.1007/s11172-021-3103-9.
   Google Scholar
• Krisyuk, B. E., and T. M. Sypko. 2021b. New thermolysis routes of diaminodinitroethylene (DADNE). Propellants, Explosives, Pyrotechnics 46:1079–96. doi:10.1002/prep.202000324.
   Web of Science ®Google Scholar
• Krisyuk, B. E., and V. S. Veretin. 2017. About some primary reactions of thermolysis of 1,1-Diamino-2,2-Dinitroethylene(FOX-7) revealed by DFT calculations. Part 1. Direct hydrogen transfer to nitro group. Butlerov Comm 49:31–35.
   Google Scholar
• Krisyuk, B. E., V. V. Zakharov, and N. V. Chukanov. 2020. On the mechanism of thermal decomposition of 1,1-Diamino-2,2-Dinitroethene (Fox-7) and its cyclic derivatives. Central European Journal of Energetic Materials 17:20–30. doi:10.22211/cejem/118513.
   Web of Science ®Google Scholar
• Krisyuk, B. E. 2020. Quantum chemical calculation of the primary thermolysis reactions of 1,1-diamino-2,2-dinitroethylene (FOX-7). Russian Chemical Bulletin 69 (12):2256–64. doi:10.1007/s11172-020-3046-6].
   Web of Science ®Google Scholar
• Latypov, N. V., J. Bergman, A. Langlet, U. Wellmar, and U. Bemm. 1998. Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene. Tetrahedron 54:11525–36. doi:10.1016/S0040-4020(98)00673-5.
   Web of Science ®Google Scholar
• Nair, U. R., S. N. Asthana, R. A. Subhananda, and B. R. Gandhe. 2010. Advances in high energy materials. Defence Science Journal 60:137–51. doi:10.14429/dsj.60.327.
   Web of Science ®Google Scholar
• Nazin, G. M., V. V. Dubikhin, T. K. Goncharov, A. I. Kazakov, A. V. Nabatova, and A. V. Shastin. 2021. Кинетика разложения 1,1-диамино-2,2-динитроэтилена (FOX-7). 1. Природа первой стадии разложения. Химическая физика 40 (6):54–65. doi:10.31857/S0207401X21060121.
   Google Scholar
• Petterson, A., P. Goede, A. Kjellstrom, and S. Wallin. 2004. Mass spectrometric study of FOX-7 decomposition. Report 1319, FOI – Swedish Defence Research Agency.
   Google Scholar
• Sikder, A. K., and N. A. Sikder. 2004. Review of advanced high performance, insensitive and thermally stable energetic materials emerging for military and space applications. Journal of Hazardous Materials 112:1–15. doi:10.1016/j.jhazmat.2004.04.003.
   PubMed Web of Science ®Google Scholar
• Sinditskii, V. P., A. I. Levshenkov, V. Y. Egorshev, and V. V. Serushkin. 2003. Study on combustion and thermal decomposition of 1,1-Diamino-2,2-dinitroethylene (FOX-7). Proc. 8th Inter. Seminar EuroPyro2003 & 30th Inter. Pyrotechnics Seminar 1:299–311.
   Google Scholar
• Trzciński, W. A., S. Cudziło, Z. Chyłek, and L. Szymańczyk. 2008. Detonation properties of 1,1-diamino-2,2-dinitroethene (dadne). Journal of Hazardous Materials 157:605–12. doi:10.1016/j.jhazmat.2008.01.026.
   PubMed Web of Science ®Google Scholar
• Zakharov, V. N., N. V. Chukanov, A. D. Chervonnyi, S. V. Vozchikova, B. L. Korsunskii, S. Yuanjie, and C. Zhiqun. 2016b. Kinetics of direct and reverse polymorphic transformations in molecular crystals of energetic compounds. Russian Chemical Bulletin, International Edition 65:91-97. doi:10.1007/s11172-016-1269-3.
   Web of Science ®Google Scholar
• Zakharov, V. V., N. V. Chukanov, A. D. Chervonnyi, S. A. Vozchikova, and B. L. Korsounskii. 2014. Kinetics of reversible polymorphic transition in energetic materials. Phase transitions α → β and β → α in 1,1-diamino-2,2-dinitroethylene. Russian Journal of Physical Chemistry B 8 (6):822–28. doi:10.1134/S1990793114110104.
   Web of Science ®Google Scholar
• Zakharov, V. V., N. V. Chukanov, N. N. Dremova, A. I. Kazakov, N. N. Volkova, A. D. Chervonnyi, B. L. Korsounskii, and G. V. Shilov. 2016a. High-temperature structural transformations of 1,1-diamino-2,2-dinitroethene (FOX-7). Propellants, Explosives, Pyrotechnics 41:2006–12. doi:10.1002/prep.201600071.
   Web of Science ®Google Scholar