Furazan-functionalized tetrazolate-based salts: A new family of insensitive energetic materials

Chemistry - A European Journal

Volumn 15, Issue 11, 2009, Pages 2625-2634

  Wang, Ruihu ^a   Guo, Yong ^b   Zeng, Zhuo ^b   Twamley, Brendan ^b   Shreeve, Jean'ne M ^b  

^a FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

^b UNIVERSITY OF IDAHO   (United States)

Author keywords

Ab initio calculations; Energetic salts; Explosives; Furazan; Nitrogen heterocycles

Indexed keywords

AMINES; BARIUM; MELTING POINT; THERMODYNAMIC STABILITY;

AB INITIO CALCULATIONS; AQUEOUS SOLUTIONS; BARIUM SALTS; DETONATION PRESSURES; DIRECT TREATMENTS; ENERGETIC SALTS; FUNCTIONALIZED; FURAZAN; HEATS OF FORMATIONS; HYPERGOLICITY; IN-SITU; INSENSITIVE ENERGETIC MATERIALS; LEWIS BASE; METATHESIS REACTIONS; NITROGEN HETEROCYCLES; PHYSICO-CHEMICAL PROPERTIES; SINGLE-CRYSTAL X-RAY ANALYSIS; SPECIFIC IMPULSE; SULFATE SALTS; TETRAZOLE; THERMAL STABILITIES;

SALTS;

EID: 62349140532     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802160     Document Type: Article

References (84)

1. a) J. P. Agrawal, Prog. Energy Combust. Sci. 1998, 24, 1-30;
2. b) D. E. Chavez, M. A. Hiskey, R. D. Gilardi, Angew. Chem. 2000, 112, 1861-1863:
3. Angew. Chem. Int. Ed. 2000, 39, 1791-1793;
4. c) M. H. V. Huynh, M. A. Hiskey, D. E. Chavez, D. L. Naud, R. D. Gilardi, J. Am. Chem. Soc. 2005, 127, 12537-12543:
5. d) M. Smiglak, A. Mellen, R. D. Rogers, Acc. Chem. Res 2001, 40, 1182-1192;
6. e) R. P. Singh, R. D. Verma, D. T. Meshri, J. M. Shreeve, Angew. Chem. 2006, 118, 3664-3682:
7. Angew. Chem. Int. Ed. 2006, 45, 3584-3601.
8. a) L. E. Fried, M. R. Manaa, P. F. Pagoria, R. L. Simpson, Annu. Rev. Mater. Res. 2001, 31, 291-321;
9. b) M. W. Schmidt, M. S. Gordon, J. A. Boatz, J. Phys. Chem. A 2005, 109, 7285-7295;
10. c) C. B. Jones, R. Haiges, T. Schroer, K. O. Christe, Angew. Chem. 2006, 118, 5103-5106; Angew. Chem. Int. Ed. 2006, 45, 4981-4984.
11. a) A. K. Zelenin, M. L. Trudell, R. D. Gilardi, J. Heterocycl. Chem. 1998, 35, 151-155;
12. b) A. B. Sheremelev, N. S. Aleksandrova. Russ. Chem. Bull. 2005, 54, 1715-1719.
13. a) A. B. Sheremetev, V. O. Kulagina, N. S. Aleksandrova, D. E. Dmitriev, Y. A. Strelenko, V. P. Lebedev, Y. N. Malyushin, Propellants Explos. Pyrotech., 1998, 23, 142-149;
14. b) S. D. Shaposhnikov, N. V. Korobov, A. V. Sergievskii, S. V. Pirogov, S. F. Mel'nikova, I. V. Tselinskii, Russ. J. Org. Chem. 2002, 38, 1351-1355.
15. A. V. Sergievskii, T. V. Romanova, S. F. Mel'nikova, I. V. Yselinskii, Russ. J. Org. Chem. 2005, 41, 261-267.
16. A. B. Sheremelev, I. L. Yudin, Mendeleev Commun. 2002, 12, 66-67.
17. a) Z. X. Li, S. Q. Tang, Y. X. Ou, B. R. Chen, J. Energ. Mater. 2002, 10, 59-65;
18. b) X. G. Zhang, H. Zhu, W. Zhang, J. Q. Zhang, S. Q. Yang, Chem. Prop. Poly. Mater. 2006, 3, 1-5.
19. a) S. D. Shaposhnikov, N. V. Korobov, A. V. Sergievskii, S. V. Pirogov, S. F. Mel'nikova, I. V. Tselinskii, Russ. J. Org. Chem. 2002, 38, 1351-1355;
20. b) J. C. Bottaro, M. A. Petrie, P. E. Penwell, D.C. Bomberger. PCT Int. Appl. 2003; WO0306371A1;
21. c) P. H. Olesen, A. R. Sørebsen, B. Ursø, P. Kurtzhals, A. N. Bowler, U. Ehrbar, B. F. Hansen, J. Med. Chem. 2003, 46, 3333-3341;
22. d) J.H. Come, J. Green, C. Marhefka, S. L. Harbeson, L. Pham. US 7157476 B2, 2007.
23. a) G. W. Drake, T. Hawkins, A. Brand, L. Hall, M. Mckay. Propellants Explos Pyrotech. 2003, 28, 174-180:
24. b) G. W. Drake, T. W. Hawkins, L. A. Hall, J. A. Boatz, A. J. Brand. Propellants Exptos. Pyrotech. 2005, 30, 329-337.
25. a) A. R. Katritzky, S. Singh, K. Kirichenko, J. D. Holbrey, M. Smiglak, W. M. Reichert, R. D. Rogers, Chem. Commun. 2005, 868-870;
26. b) A. R. Katritzky, H. Yang, D. Zhang, K. Kirichenko, M. Smiglak. J. D. Holbrey, W. M. Reichert, R. D. Rogers, New J. Chem. 2006, 30, 349-358:
27. c) A. R. Katritzky, S. Singh, K. Kirichenko, M. Smiglak. J. D. Holbrey, W. M. Reichert, S. K. Spear, R. D. Rogers, Chem. Eur. J. 2006, 12, 4630-4641.
28. a) C. Ye, H. Gao, J. A. Boatz, G. W. Drake, B. Twamley, J. M. Shreeve, Angew. Chem. 2006, 118, 7420-7423;
29. Angew. Chem. Int. Ed. 2006, 45. 7262-7265:
30. b) 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;
31. c) R. Wang, H. Gao, C. Ye, J. M. Shreeve, Chem. Mater. 2007, 19, 144-152;
32. d) Y. H. Joo, B. Twamley, S. Garg, J. M. Shreeve, Angew. Chem. 2008, 120, 6332-6335; Angew. Chem. Int. Ed. 2008, 47, 6236-6239:
33. e) T. Abe, G. H. Tao, Y. H. Joo, Y. Huang, B. Twamley, J. M. Shreeve, Angew. Chem. 2008, 120, 7195-7198: Angew. Chem. Int. Ed. 2008, 47, 7087-7090.
34. a) H. Xue, B. Twamley, J. M. Shreeve, Adv. Mater. 2005, 17, 2142-2146;
35. b) C. F. Ye, J. C. Xiao, B. Twamley, J. M. Shreeve, Chem. Commun. 2005, 2750-2752:
36. c) C. M. Jin, C. F. Ye, C. Piekarski, B. Twamley, J. M. Shreeve, Eur. J. Inorg. Chem. 2005, 3760-3767;
37. d) Y. Guo, H. Gao, B. Twamley, J. M. Shreeve, Adv. Mater. 2007, 19, 2884-2888:
38. e) R. Wang, H. Gao, C. Ye, B. Twamley, J. M. Shreeve, Inorg. Chem. 2007, 46, 932-938:
39. f) Z. Zeng, H. Gao, B. Twamley, J. M. Shreeve, J. Mater. Chem. 2007, 17, 3819-3826;
40. g) H. Xue, H. Gao, B. Twamley. J. M. Shreeve, Chem. Mater. 2007, 19, 1731-1739;
41. h) H. Gao, Y. Huang, C. Ye, B. Twamley, J. M. Shreeve, Chem. Eur. J. 2008, 14, 5596-5603.
42. a) T. M. Klapötke, P. Mayer, A. Schulz, J. J. Weigand, J. Am. Chem. Soc. 2005, 127, 2032-2033;
43. b) G. Steinhäuser, T. M. Klapölke, Angew. Chem. 2008, 120, 3376-3394;
44. Angew. Chem. Int. Ed. 2008, 47, 3330-3347:
45. c) C. Darwich, T.M. Klapötke, C. MiróSabalé, Chem. Eur. J. 2008, 14, 5756-5771.
46. a) J. C. Gálvez-Ruiz, G. Holl, K. Karaghiosoff, T. M. Klapölke, K. Löhnwitz, P. Mayer, H. Nöth, K. Polborn, C. J. Rohbogner, M. Suter, J. J. Weigand, Inorg. Chem. 2005, 44, 4237-4253;
47. b) K. Konstantin, T. M. Klapötke, P. Mayer, H. Piotrowski, K. Polborn, R. L. Willer, J. J. Weigand, J. Org. Chem. 2006, 71, 1295-1305:
48. c) T. M. Klapötke, K. Karaghiosoff, P. Mayer, A. Penger, J. M. Welch, Propellants, Propellants Explos. Pyrotech. 2006, 31, 188-195;
49. d) T. M. Klapötke, J. Stierstorfer, Helv. Chim. Acta 2007, 90, 2132-2150;
50. e) T. M. Klapötke, P. Mayer, C. MiróSabaté, J. M. Welch, N. Wiegand, Inorg. Chem. 2008, 47, 6014-6027;
51. f) K. Karaghiosoff, T. M. Klapötke, P. Mayer, C. MiróSabaté, A. Penger, J. M. Welch, Inorg. Chem. 2008, 47, 1007-1019;
52. g) T. M. Klapölke, C. MiróSabaté, Chem. Mater. 2008, 20, 3629-3637;
53. h) T. M. Klapötke, J. Slierstorfer, A. U. Wallek, Chem. Mater. 2008, 20, 4519-4530;
54. i) T. M. Klapötke, C. MiróSabalé, Chem. Mater. 2008, 20, 1750-1763.
55. a) C. E. Stoner, Jr., A. L. Rheingold, T. B. Brill, Inorg. Chem. 1991, 30, 360-364;
56. b) A. B. Sheremelev, V. O. Kulagina, I. A. Kryazhevskikh, T. M. Melnikova, N. S. Aleksandrova, Russ. Chem. Bull. 2002, 57, 1533-1539;
57. c) M. B. Talawar, R. Sivabalan, N. Senlhilkumar, G. Prabhu, S. N. Asthana, J. Hazardous Mater. A 2004, 113, 11-25.
58. R. L. Willer, R. S. Day, D. J. Park, US 5460669, 1995.
59. S. D. Shaposhnikov, T. V. Romanova, N. P. Spiridonova, S. F. Mel'nikova, I. V. Tselinskii, Russ. J. Org. Chem. 2004, 40, 884-888.
60. C. Zhang, J. Mol. Struct. 2006, 765, 77-83, and references therein.
61. a) T. Ichikawa, T. Kato, T. Takenishi, J. Heterocycl. Chem. 1965, 2, 253-255:
62. b) V. G. Andrianov, A. V Eremeev, Khimiya Geterotsiklicheskikh Soedinenii 1994, 693-696:
63. c) J. H. Come, J. Green, C. Marhefka, S. L. Harbeson, L. Pham, PCT Int. Appl. 2005, WO 2005019190.
64. K. R. Seddon, J. Chem. Technol. Biotechnol. 68, 351-356.
65. a) C. Ye, J. M. Shreeve, J. Phys. Chem. A 2007, 111, 1456-1461:
66. b) C. Ye, J. M. Shreeve, J. Chem. Eng. Data 2008, 53, 520-524.
67. S. Schneider, T. Hawkins, M. Rosander, G. Vaghjiani, S. Chambreau, G. Drake, Energy Fuels 2008, 22, 2871-2872.
68. a) M. W. Schmidt, M. S. Gordon, J. A. Boalz, J. Phys. Chem. A 2005, 109, 7285-7295:
69. b) K. E. Gutowski, J. D. Holbrey, R. D. Rogers, D. A. Dixon J. Phys. Chem. B 2005, 109, 23196-23208:
70. c) K. E. Gutowski, R. D. Rogers, D. A. Dixon, J. Phys. Chem. B 2007, 111, 4788-4800;
71. d) H. Gao, C. Ye, C. Piekarski, J. M. Shreeve J. Phys. Chem. C. 2007, 111, 10718-10731.
72. a) L. E. Fried, K. R. Glaesemann and W. M. Howard, P. C. Souers, CHEETAH 5.0 User's Manual., Lawrence Livermore National Laboratory, 2007;
73. b) J. P. Lu, Evaluation of the Thermochemical Code -CHEETAH 2.0 for Modelling Explosives Performance, Edinburgh, 2001.
74. Gaussian 03, Revision D.01, M. J. Frisch, G.W. Tracks, 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. Pelersson, H. Nakalsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Kiene, 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., Wall-ingford CT. 2004.
75. H. D. B. Jenkins, D. Tudeal, L. Glasser, Inorg. Chem. 2002, 41, 2364-2367.
76. SMART: V.5.626. Bruker Molecular Analysis Research Tool, Bruker AXS, Madison, 2002.
77. SAINTPlus: V. 6.45a. Data Reduction and Correction Program, Bruker AXS. Madison, 2003.
78. SADABS: V.2.01, an empirical absorption correction program, Bruker AXS Inc. Madison, 2004.
79. G. M. Sheldrick. SHELXTL: V. 6.10, Structure Determination Software Suite. Bruker AXS Inc. Madison, 2001.
80. Bruker, APEX2 v2.1-0, Bruker AXS Inc., Madison, 2006
81. Bruker, SAINT v7.34A, Bruker AXS Inc., Madison, 2005.
82. Bruker, SADABS v2004/1. Bruker AXS Inc., Madison, 2004.
83. Bruker, XPREP v6.12. Bruker AXS Inc., Madison, 2001.
84. Bruker, SHELXTL v6.12. Bruker AXS Inc., Madison, 2000.