4-nitro-3-(5-tetrazole)furoxan and its salts: Synthesis, characterization, and energetic properties

Chemistry - A European Journal

Volumn 19, Issue 44, 2013, Pages 14902-14910

  Liang, Lixuan ^a   Wang, Kai ^a   Bian, Chengming ^a   Ling, Liming ^a   Zhou, Zhiming ^a  

^a BEIJING INSTITUTE OF TECHNOLOGY   (China)

Author keywords

detonation performance; energetic materials; furoxan; nitrogen heterocycles; X ray diffraction

Indexed keywords

DETONATION PERFORMANCE; DETONATION PRESSURE; ENERGETIC PROPERTIES; FUROXAN; IMPACT SENSITIVITIES; NITROGEN HETEROCYCLES; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; THEORETICAL PERFORMANCE;

CHARACTERIZATION; DETONATION; DIFFERENTIAL SCANNING CALORIMETRY; EXPLOSIVES; HAMMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

SALTS;

EID: 84885861894     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301042     Document Type: Article

References (66)

1. V. Zelenak, Z. Vargova, K. Gyoryova, E. Vecernikova, V. J. Balek, J. Therm. Anal. Calorim. 2005, 82, 747-754
2. M. X. Zhang, P. E. Eaton, R. D. Gilardi, Angew. Chem. 2000, 112, 422-426
3. Angew. Chem. Int. Ed. 2000, 39, 401-404
4. D. E. Chavez, M. A. Hiskey, R. D. Gilardi, Angew. Chem. 2000, 112, 1861-1863
5. Angew. Chem. Int. Ed. 2000, 39, 1791-1793
6. D. E. Chavez, M. A. Hiskey, R. D. Gilardi, Org. Lett. 2004, 6, 2889-2891.
7. H. Gao, C. Ye, O. D. Gupta, J. C. Xiao, M. A. Hiskey, B. Twamley, J. M. Shreeve, Chem. Eur. J. 2007, 13, 3853-3860.
8. A. R. Katritzky, S. Singh, K. Kirichenko, J. D. Holbrey, M. Smiglak, W. M. Reichert, R. D. Rogers, Chem. Commun. 2005, 868-870.
9. H. Xue, B. Twamley, J. M. Shreeve, Adv. Mater. 2005, 17, 2142-2146.
10. M. Hiskey, N. Goldman, J. Stine, J. Energ. Mater. 1998, 16, 119-127
11. S. Löbbecke, A. Pfeil, H. H. Krause, J. Sauer, U. Holland, Propellants Explos. Pyrotech. 1999, 24, 168-175
12. A. Hammerl, G. Holl, M. Kaiser, T. M. Klapötke, P. Mayer, H. Piotrowski, M. Suter, Z. Naturforsch, B: Chem. Sci. 2001, 56, 857-870
13. A. Kraft, L. Peters, R. Frölich, Acta Crystallogr. Sect. C 2002, 58, o 272 -o 274
14. A. Hammerl, G. Holl, T. M. Klapötke, P. Mayer, H. Noth, H. Piotrowski, M. Warchhold, Eur. J. Inorg. Chem. 2002, 834-845.
15. H. X. Gao, R. Wang, B. Twamley, M. A. Hiskey, J. M. Shreeve, Chem. Commun. 2006, 4007-4009.
16. R. Wang, Y. Guo, Z. Zeng, B. Twamley, J. M. Shreeve, Chem. Eur. J. 2009, 15, 2625-2634.
17. A. B. Sheremetev, I. L. Yudin, N. V. Palysaeva, K. Y. Suponitsky, J. Heterocycl. Chem. 2012, 49, 394-401.
18. A. Gasco, R. Fruttero, G. Sorba, A. DiStilo, R. Calvino, Pure Appl. Chem. 2004, 76, 973
19. M. Boiani, H. Cerecetto, M. Gonzalez, M. Risso, C. Olea-Azar, O. Piro, E. E. Castellano, A. L. Cerain, O. Ezpeleta, A. Monge-Vega, Eur. J. Med. Chem. 2001, 36, 771
20. C. Cena, S. Visentin, A. DiStilo, D. Boschi, R. Fruttero, A. Gasco, Pharm. Res. 2001, 18, 157.
21. B. T. Federoff, Encyclopedia of Explosives and Related Items, Picatinny Arsenal, Dover, 1962
22. Y. Oyumi, T. B. Brill, Combust. Flame 1986, 65, 313
23. B. M. Rice, J. J. Hare, J. Phys. Chem. A 2002, 106, 1770.
24. A. B. Sheremetev, J. Heterocycl. Chem. 1995, 32, 371
25. T. S. Pivina, D. V. Sukhachev, A. V. Evtushenko, L. I. Khmelnitskii, Propellants Explos. Pyrotech. 1995, 20, 5
26. A. B. Sheremetev, N. S. Aleksandrova, E. V. Mantseva, D. E. Dmitriev, Mendeleev Commun. 2000, 10, 67
27. A. B. Sheremetev, E. V. Mantseva, Mendeleev Commun. 1996, 6, 244
28. A. B. Sheremetev, E. V. Mantseva, D. E. Dmitriev, F. S. Sirovskii, Russ. Chem. Bull. Int. Ed. 2002, 51, 659-662
29. A. M. Churakov, S. E. Semenov, S. L. Ioffe, Y. A. Strelenko, V. A. Tartakovskii, Mendeleev Commun. 1995, 5, 102.
30. W. Zheng, J. Wang, X. Ren, Z. Chen, J. Tian, Y. Zhou, J. Hazard. Mater. 2010, 177, 738-742.
31. C. Zhang, J. Mol. Struct. THEOCHEM. 2006, 765, 77-83.
32. L. Liang, H. Huang, K. Wang, C. Bian, J. Song, L. Ling, F. Zhao, Z. Zhou, J. Mater. Chem. 2012, 22, 21954.
33. H. Huang, Z. Zhou, L. Liang, J. Song, K. Wang, D. Cao, C. Bian, W. Sun, M. Xue, Z. Anorg. Allg. Chem. 2012, 638, 392-400
34. H. Huang, Z. Zhou, L. Liang, J. Song, K. Wang, D. Cao, W. Sun, C. Bian, M. Xue, Chem. Asian J. 2012, 7, 707-714.
35. A. Marshall, Explosives, J. and A. Churchill, London, 1917
36. H. Brunswig, Explosives, Wiley, New York, 1912
37. J. Akhavan, The Chemistry of Explosives, Royal Society of Chemistry, Cambridge, 2004.
38. W. S. McEwan, M. W. Rigg, J. Am. Chem. Soc. 1951, 73, 4725-4727.
39. Y. Luo, L. Ma, B. Wang, Y. Zhou, H. Huo, S. Jia, Chin. J. Energ. Mater. 2010, 18, 538-540.
40. Z. P. Demko, K. B. Sharpless, J. Org. Chem. 2001, 66, 7945-7950.
41. M. D. Coburn, J. Heterocycl. Chem. 1968, 5, 83
42. R. Calvino, V. Motrarini, A. Gasco, A. Sanfilippo, M. L. Ricciardi, Eur. J. Med. Chem. -Chim, Therap. 1980, 15, 485
43. G. D. Solodyuk, M. D. Boldyrev, B. V. Gidaspov, V. D. Nikolaev, Zh. Org. Khim. 1981, 17, 861
44. M. D. Coburn, J. Heterocycl. Chem. 1986, 23, 421
45. A. B. Sheremetev, O. V. Kharitonova, Mendeleev Commun. 1992, 2, 157
46. T. S. Novikova, T. M. Mel'nikova, A. B. Sheremetev, Mendeleev Commun. 1994, 4, 138-140.
47. H. Huang, Z. Zhou, J. Song, L. Liang, K. Wang, D. Cao, W. Sun, X. Dong, M. Xue, Chem. Eur. J. 2011, 17, 13593-13602.
48. www.bam.de
49. M. W. Schmidt, M. S. Gordon, J. A. Boatz, J. Phys. Chem. A 2005, 109, 7285-7295
50. K. E. Gutowski, R. D. Rogers, D. A. Dixon, J. Phys. Chem. B 2007, 111, 4788-4800
51. K. E. Gutowski, J. D. Holbrey, R. D. Rogers, D. A. Dion, J. Phys. Chem. B 2005, 109, 23196-23208
52. H. Gao, C. Ye, C. Piekarski, J. M. Shreeve, J. Phys. Chem. C 2007, 111, 10718-10731
53. X. Zhang, W. Zhu, T. Wei, C. Zhang, H. Xiao, J. Phys. Chem. C 2010, 114, 13142-13152.
54. Gaussian03, RevisionE.01, 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. Strain, 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, 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, Inc., Wallingford CT, 2004.
55. Y. Guo, G. Tao, Z. Zeng, H. Xiang, D. A. Parrish, J. M. Shreeve, Chem. Eur. J. 2010, 16, 3753-3762
56. R. Wang, H. Xu, Y. Guo, R. Sa, J. M. Shreeve, J. Am. Chem. Soc. 2010, 132, 11904-11905
57. G. H. Tao, Y. Guo, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. 2010, 20, 2999-3005
58. H. Xue, H. Gao, B. Twamley, J. M. Shreeve, Chem. Mater. 2007, 19, 1731-1739.
59. M. Suc̈eska, EXPLO5.05 program, Zagreb, 2011.
60. M. J. Kamlet, S. J. Jacobs, J. Chem. Phys. 1968, 48, 23-35
61. M. J. Kamlet, J. E. Ablard, J. Chem. Phys. 1968, 48, 36-42
62. M. J. Kamlet, C. Dickinson, J. Chem. Phys. 1968, 48, 43-49.
63. F. H. Allen, R. Taylor, D. G. Watson, O. Kennard, A. G. Orpen, International Table for Crystallography. Kluwer Academic Publishers, Dordrecht, 1992.
64. K. Karaghiosoff, T. M. Klapötke, C. M. Sabaté, Eur. J. Inorg. Chem. 2009, 238-250.
65. CrystalClear: SM Expert 2.0 r2, An Integrated Program for the Collection and Processing of Area Detector Data, Rigaku Corporation, England, 2009.
66. G.M. Sheldrick, SHELXTL-97, Structure Determination Software Suite, Bruker AXS, Madison, 2008.