Abstract
Modeling of the probable mechanisms of the thermolysis of C-and N-nitramino-1,2,4-triazoles has been carried out by methods of mathematical chemistry. It was established that the formation is possible of a more diverse spectrum of products in their destruction than was previously recorded by different experimental methods. Subsequent assessment of the thermochemical preference for pathways of decomposition of the compounds was carried out by the density functional method in the B3LYP/6-31G* approach. It was determined that the thermal destruction of C-and N-nitramino-substituted polynitrogen heterocycles, capable of tautomeric conversion, was most probably through the thermochemically least stable nitramine form. Thermal decomposition of the considered tautomers is preferred at the NNO2 fragment and not at the triazole ring. The direction of the structural stabilization of the investigated compounds has been clarified by comparison of the geometric, electronic, and thermochemical characteristics of C-NNO2-and N-NNO2-substituted 1,2,4-triazoles.
Similar content being viewed by others
References
G. B. Manelis, G. M. Nazin, Yu. I. Rubtsov, and V. A. Strunin, Thermal Decomposition and Combustion of Explosive Substances and Gunpowder [in Russian], Nauka, Moscow (1996).
L. P. Smirnov, Usp. Khim., 73, 1210 (2004).
L. P. Smirnov, in: Energetic Condensed Systems. All-Russian Conference,2–12 November 2004, Chernogolovka, 2004, p. 72.
V. F. Sopin and G. A. Marchenko, in: Contemporary Problems of Technical Chemistry. All-Russian Conference, 21–22 November 2003, Kazan 2003, p. 40.
P. Politzer and J. S. Murray, in: P. L. Marinkas (editor), Organic Energetic Compounds, Nova Sci. Publ. Inc., New York (1996), p. 1.
G. A. Olah and R. Squire, in: G. A. Olah (editor), Chemistry of Energetic Materials, Acad. Press, San Diego (1991), p. 212.
J. Kohler and R. Meyer, Explosives, 4_rev. and extended ed., VCH, Weinheim (1993), p. 457.
P. L. Marinkas in: P. L. Marinkas (editor), Organic Energetic Compounds, Nova Sci. Publ. Inc., New York (1996), p. 425.
P. Politzer, P. Lane, and M. C. Concha in: P. Politzer and J. S. Murray (editors), Theoretical and Computational Chemistry 12 (Energetic Materials, Pt I), Elsevier, London, New York (2003), p. 247.
A. A. Porollo, D. E. Lushnikov, T. S. Pivina, V. P. Ivshin, J. Mol. Struct. (THEOCHEM), 391, 117 (1997).
A. A. Porollo, D. E. Lushnikov, T. S. Pivina, V. P. Ivshin, and N. S. Zefirov, Izv. Akad. Nauk, Ser. Khim., 1869 (1999).
A. A. Porollo, T. V. Petukhova, V. P. Ivshin, T. S. Pivina, and D. E. Lushnikov, in: Proc. 30th Int. Ann. Conf. ICT. Energetic Materials: Reactions of Propellants, Explosives and Pyrotechnics, Karlsruhe, Germany 1999, p. 15/1.
T. S. Pivina, A. A. Porollo, T. V. Petukhova, and V. P. Ivshin, in: Proc. 26th Int. Pyrotechnics Seminar, Nanjing, China, 1999, p. 438.
T. S. Pivina, A. A. Porollo, T. V. Petukhova, and V. P. Ivshin, in: Proc. 5th Int. Symp. Special Topics in Chemical Propulsion (5-ISICP), Italy, 2000, p. 343.
A. A. Porollo, T. V. Petukhova, V. P. Ivshin, T. S. Ivshina, and E. A. Smolenskii, in: Abstracts 2nd All-Russian Conf. on Molecular Modeling, Moscow, 2001, p. 94.
A. A. Porollo, T. V. Petukhova, V. P. Ivshin, T. S. Pivina, B. L. Korsunskii, and O. Golovanov, in: Proc. 32nd Int. Ann. Conf. ICT, Energetic Materials: Reactions of Propellants, Explosives and Pyrotechnics, Karlsruhe, Germany, 2001, p. 87/1.
T. V. Petukhova, A. A. Porollo, V. L. Korolev, V. P. Ivshin, Y. N. Surikova, and T. S. Pivina, in: Proc. 33rd Int. Ann. Conf. ICT, Energetic Materials: Reactions of Propellants, Explosives and Pyrotechnics, Karlsruhe, Germany, 2002, p. 60/1.
V. L. Korolev, T. V. Petukhova, T. S. Pivina, A. A. Porollo, A. B. Sheremetev, K. Yu. Suponitskii, and V. P. Ivshin, Izv. Akad. Nauk, Ser. Khim., 1338 (2006).
M. S. Pevzner, Ros. Khim. Zh., 41, 73 (1997).
A. B. Sheremetev, Ros. Khim. Zh., 41, 43 (1997).
H. H. Licht, S. Braun, M. Wanders, and H. Ritter, in: Proc. 29th Int. Ann. Conf. ICT, Energetic Materials: Reactions of Propellants, Explosives and Pyrotechnics, Karlsruhe, Germany, 1998, p. 47/1.
V. L. Korolev, T. V. Petukhova, T. S. Pivina, A. B. Sheremetev, A. E. Miroshnichenko, and V. P. Ivshin, Khim. Geterotsikl. Soedin., 1817 (2004). [Chem. Heterocycl. Comp., 40, 1568 (2004).
A. M. Astachov, V. A. Revenko, and E. S. Buka, in: Proc. 7th Seminar on New Trends in Research of Energetic Materials, Pardubice, Czech Republic, 2004, p. 424.
V. A. Myasnikov, V. A. Vyazkov, I. L. Yudin, O. P. Shitov, and V. A. Tartakovskii, Izv. Akad. Nauk, Ser. Khim., 1239 (1991).
V. A. Tartakovsky, in: Decomposition, Combustion, and Detonation Chemistry of Energetic Materials, Symposium, November 27–30, 1995, Boston, Mass., USA. T. B. Brill, T. P. Russell, W. C. Tao, and R. B. Wardle (editors), Materials Research Society Symposium Proceedings, Vol. 418, p. 15.
A. Gao, A. L. Reingold, and T. B. Brill, Propellants, Explosives, Pyrotechnics, 16, 97 (1991).
T. B. Brill and T. B. Patil, Thermochim. Acta, 235, 225 (1994).
A. M. Astakhov, Dissertation for Candidate of Chemical Sciences, Siberian State Technological University, Krasnoyarsk, 1999, 118 pp.
R. S. Stepanov, A. M. Astachov, and L. A. Kruglova, in: Proc. 34th Int. Ann. Conf. ICT, Energetic Materials: Reactions of Propellants, Explosives and Pyrotechnics, Karlsruhe, Germany, 2003, p. 53/1.
A. A. Nefedov, Dissertation for Candidate of Chemical Sciences, Siberian State Technological University, Krasnoyarsk, 2004, 150 pp.
E. V. Sokerina, D. E. Lushnikov, T. S. Pivina, A. A. Porollo, and V. P. Ivshin, in: Proc. 21st Int. Pyrotechnics Seminar, Moscow, 1995, p. 849.
A. A. Porollo, Dissertation for Candidate of Chemical Sciences, Mari State University, Ioshkar-Ola, 1999, 135 pp.
T. V. Petukhova, Dissertation for Candidate of Chemical Sciences, Mari State University, Ioshkar-Ola, 2004, 136 pp.
W. Koch and M. C. Holthausen, A Chemist’s Guide to Density Functional Theory, Wiley-VCH, Weinheim (2001), 300 pp.
T. Clark, A Handbook of Computational Chemistry, J. Wiley & Sons, New York (1985).
Gaussian 98 Program Set, Center for Computer Provision for Chemical Investigations, Russian Academy of Sciences.
E. D. Raczynska, R. Kosinska, B. Osmialowski, and R. Gawinecki, Chem. Rev., 105, 3561 (2005).
J. Elguero, A. R. Katritzky, and O. V. Denisenko, Adv. Heterocycl. Chem., 76, 1 (2001).
V. I. Minkin, A. D. Garnovskii, J. Elguero, A. R. Katritzky, and O. V. Denisenko, Adv. Heterocycl. Chem., 76, 157 (2001).
I. Shcherbakova, J. Elguero, and A. R. Katritzky, Adv. Heterocycl. Chem., 77, 51 (2001).
V. G. Avakyan and O. V. Fateev, Izv. Akad. Nauk, Ser. Khim., 100 (1993).
A. L. Fridman, V. P. Ivshin, and S. S. Novikov, Usp. Khim., 38, 1448 (1969).
G. Foiera (editor), Chemistry of Nitro and Nitroso Groups [Russian translation], Mir, Moscow (1972).
S. S. Novikov, V. V. Sevost’yanova, and V. A. Shlyapochnikov, Chemistry of Aliphatic and Alicyclic Nitro Compounds [in Russian], Khimiya, Moscow (1974).
Yu. A. Orlova, Chemistry and Technology of High Explosives [in Russian], Khimiya, Leningrad (1980).
T. P. Kofman, G. Yu. Kartseva, and M. B. Shcherbinin, Zh. Org. Khim., 38, 1397 (2002).
H. H. Licht and H. Ritter, J. Energ. Mat., 12, 223 (1994).
J. E. De Vries and E. St. Clair Gantz, J. Am. Chem. Soc., 1008 (1954).
Zh. N. Fidler, M. G. Luchina, and V. A. Lopyrev, Zh. Org. Khim., 9, 1205 (1973).
R. A. Henry, J. Am. Chem. Soc., 72, 5343 (1950).
G. I. Chipen, V. Ya. Grinshtein, and R. P. Preiman, Zh. Obshch. Khim., 32, 454 (1962).
M. S. Pevzner, T. N. Kulibabina, N. A. Povarova, and L. V. Kilina, Khim. Geterotsikl. Soedin., 1132 (1979). [Chem. Heterocycl. Comp., 15, 929 (1979)].
T. G. Bonner and J. C. Lockhart, J. Chem. Soc., 3858 (1958).
M. S. Pevzner, N. V. Gladkova, and T. A. Kravchenko, Zh. Org. Khim., 32, 1230 (1996).
A. M. Astakhov, A. D. Vasil’ev, M. S. Molokeev, V. A. Revenko, and R. S. Stepanov, Zh. Org. Khim., 41, 928 (2005).
P. Politzer, M. E. Grice, and J. M. Seminario, J. Quantum Chem., 61, 389 (1997).
A. Gao, Y. Oyumi, and T. V. Brill, Combust Flame, 83, 345 (1991).
T. V. Brill, Prog. Energy Combust. Sci., 18, 91 (1992).
T. V. Brill and H. Ramanathan, Combust Flame, 122, 165 (2000).
A. D. Vasiliev, A. M. Astachov, R. S. Stepanov, and S. D. Kirik, Acta Crystallogr., C55, 830 (1999).
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1467–1495, October, 2006.
Rights and permissions
About this article
Cite this article
Korolev, V.L., Petukhova, T.V., Bakhmatova, E.A. et al. Molecular modeling of the mechanisms of thermolysis of nitramino-1,2,4-triazoles. Chem Heterocycl Compd 42, 1267–1290 (2006). https://doi.org/10.1007/s10593-006-0236-6
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-006-0236-6