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Synthesis, Thermal Behaviours and Crystal Structure of 1,1'-Dioxide-7,7'-bis(terfurazan[3,4-b:3,4'-d:3'',4''-f]azepine)
Corresponding Author(s) : Jun Dong
Asian Journal of Chemistry,
Vol. 26 No. 21 (2014): Vol 26 Issue 21
Abstract
1,1'-Dioxide-7,7'-bis(terfurazan[3,4-b:3,4'-d:3'',4''-f]azepine) was synthesized from 3,4-bis(4-nitrofurazan-3-yl)furoxan by cyclization and nitration with a yield of 25.7 % and its structure and intermediate were characterized by 1H NMR, 13C NMR, FT-IR and elementary analysis. Its single crystal was obtained and its crystal structure was studied by X-ray single-crystal diffraction analysis. The title compound (C18H12N14O10, Mr = 584.42) crystallizes in trigonal system, P3(2) space group and constituted one 1,1'-dioxide-7,7'-bis(terfurazan[3,4-b:3,4'-d:3'',4''-f]azepine) and two acetone molecules, with a =15.460 (18), b = 15.460 (18), c = 9.603 (11) Å, V = 1988 (4) Å3, Z = 3, Dc = 1.465 g/cm3, l = 0.071073 Å, μ(MoKa) = 0.123 mm-1, F(000) = 894, S = 1.022, R = 0.0720 and wR = 0.1838. In DSC and TG-DTG techniques suggest that there are two main decomposition peaks at 288.7 and 338.7 °C. The results show that the title compound had favorable thermal stability.
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- J. Kerth and S. Löbbecke, Propellants, Explosives, Pyrotechnics, 27, 111 (2002); doi:10.1002/1521-4087(200206)27:3<111::AID-PREP111>3.0.CO;2-O.
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- M.A. Hiskey, D.E. Chavez and S.F. Son, Proc. 27th International Pyro-technics Seminar, July 16-21, Colorado, USA, pp. 3-14 (2000).
- T. Eicher, S. Hauptmann, R.T. Li, Z.M. Ge and X. Wang, Chemical Industry Press, Beijing, pp. 158-159 (2005) (in Chinese).
- A.B. Sheremetev, E.A. Ivanova, N.P. Spiridonova, S.F. Melnikova, I.V. Tselinsky, K.Y.U. Suponitsky and M.Y.U. Antipin, J. Heterocycl. Chem., 42, 1237 (2005); doi:10.1002/jhet.5570420634.
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- H.-X. Hu, G.-M. Qin and Z.-Z. Zhang, Chinese Patent, 3,4-Dinitro-furazanfuroxan Explosive: CN 02101092.7 (2002).
- Y.S. Zhou, B.Z. Wang, X.J. Wang, C. Zhou and H. Huo, Chinese J. Energet. Mater., 20, 137 (2012).
- I.S. Andrei, V.D. Dmitry and A.A. Alexander, Some Chemical Properties of 3,4-bis(4-nitro- furazan-3-yl)furoxan. Seminar in New Trends in Research of Energetic Materials, Czech Republic, pp. 301-308 (2012).
- G.M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, Germany (1997).
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References
J. Kerth and S. Löbbecke, Propellants, Explosives, Pyrotechnics, 27, 111 (2002); doi:10.1002/1521-4087(200206)27:3<111::AID-PREP111>3.0.CO;2-O.
A.M. Churakov, O.Y. Smirnov, S.L. Ioffe, Y.A. Strelenko and V.A. Tartakovsky, Eur. J. Org. Chem., 2342 (2002); doi:10.1002/1099-0690(200207)2002:14<2342::AID-EJOC2342>3.0.CO;2-H.
M.A. Hiskey, D.E. Chavez and S.F. Son, Proc. 27th International Pyro-technics Seminar, July 16-21, Colorado, USA, pp. 3-14 (2000).
T. Eicher, S. Hauptmann, R.T. Li, Z.M. Ge and X. Wang, Chemical Industry Press, Beijing, pp. 158-159 (2005) (in Chinese).
A.B. Sheremetev, E.A. Ivanova, N.P. Spiridonova, S.F. Melnikova, I.V. Tselinsky, K.Y.U. Suponitsky and M.Y.U. Antipin, J. Heterocycl. Chem., 42, 1237 (2005); doi:10.1002/jhet.5570420634.
A.M. Churakov, S.E. Semenov, S.L. loffe, Y.A. Strelenko and V.A. Tartakovskii, Mendeleev Commun., 5, 102 (1995); doi:10.1070/MC1995v005n03ABEH000477.
H.-X. Hu, G.-M. Qin and Z.-Z. Zhang, Chinese Patent, 3,4-Dinitro-furazanfuroxan Explosive: CN 02101092.7 (2002).
Y.S. Zhou, B.Z. Wang, X.J. Wang, C. Zhou and H. Huo, Chinese J. Energet. Mater., 20, 137 (2012).
I.S. Andrei, V.D. Dmitry and A.A. Alexander, Some Chemical Properties of 3,4-bis(4-nitro- furazan-3-yl)furoxan. Seminar in New Trends in Research of Energetic Materials, Czech Republic, pp. 301-308 (2012).
G.M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, Germany (1997).
G.M. Sheldrick, SHELXTS-97, Program for Crystal Structure Solution, University of Göttingen, Germany (1997).
S.-Y. Jia, B.-Z. Wang, X.-Z. Fan, P. Li and S.W. Ng, Acta Crystallogr., E68, o1573 (2012); doi:10.1107/S1600536812017825.
A.B. Sheremetev, E.A. Ivanova, D.E. Dmitriev, V.O. Kulagina, B.B. Averkiev and M.Y. Antipin, J. Heterocycl. Chem., 42, 803 (2005); doi:10.1002/jhet.5570420509.
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, 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, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Daniels, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith and M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03 (Revision A.1), Gaussian, Inc., Pittsburgh, PA (2004).