5-Aminotetrazolium 5-aminotetrazolates - New insensitive nitrogen-rich materials

Zeitschrift fur Anorganische und Allgemeine Chemie

Volumn 635, Issue 12, 2009, Pages 1812-1822

  Klapötke, Thomas M ^a   Sabaté, Carles Miró ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Crystal structures; Density functional calculations; Energetic; Heterocycles; Nitrogen rich compounds

Indexed keywords

EID: 70350341947     PISSN: 00442313     EISSN: 15213749     Source Type: Journal    
DOI: 10.1002/zaac.200801357     Document Type: Article

References (107)

1. L. V. De Yong, G. Campanella, J. Hazard. Mater. 1989, 27, 125.
2. a) Dynamit. Nobel G. m. b. H. (K. Redecker, W. Weuter, U. Bley, D. Schmittner), DE-BP. 19730873 (January 22, 1998);
3. b) Chung Shan Institute of Science & Technology (Y. Peng, C. Wong) U. S.5877300 (March 2, 1999);
4. c) M. Kaiser, U. Ticmanis, Inorg. Chem. 2001, 40, 3570;
5. d) T. M. Klapötke, C. Miró Sabaté, Heteroatom Chem. 2008, 79, 301.
6. a) Etat Francais (J. Duguet) U. S.4566921 (January 28, 1986);
7. th Seminar on New Trends in Research of Energetic Materials, Pardubice, Czech Republic, 25-27 April 2007.
8. A. K. Sikder, N. Sikder, J. Hazard. Mater. 2004, A112, 1.
9. a) T. M. Klapötke, C. Miró Sabaté, Z. Anorg. Allg. Chem. 2007, 633, 2671;
10. b) T. M. Klapötke, C. Miró Sabaté, Z. Anorg. Allg. Chem. 2008, 634, 1017;
11. c) T. M. Klapötke, C. Miró Sabaté, Eur. J. Inorg. Chem. 2008, 34, 5350;
12. d) T. M. Klapötke, P. Mayer, C. Miró Sabaté, J. M. Welch, N. Wiegand, Inorg. Chem. 2008, 47, 6014;
13. e) T. M. Klapötke, C. Miró Sabaté, J. Stierstorfer, New J. Chem. 2008, 32, 1.
14. a) Y. Guo, H. Gao, B. Twamley, J. M. Shreeve, Adv. Mater. 2007, 19, 2884;
15. b) H. Xue, H. Gao, B. Twamley, J. M. Shreeve, Chem. Mater. 2007, 19, 1731;
16. c) Z. Zeng, H. Gao, B. Twamley, J. M. Shreeve, J. Mater. Chem. 2007, 17, 3819;
17. d) H. Gao, Y. Huang, C. Ye, B. Twamley, J. M. Shreeve, Chem. Eur. J. 2008, 14, 5596.
18. rd International Annual Conference of ICT, Karlsruhe, Germany, 2002, 62, 1;
19. b) A. Vij, J. G. Pavlovich, W. W. Wilson, V. Vij, K. O. Christie, Angew. Chem. 2002, 114, 3177;
20. Angew. Chem. Int. Ed. 2002, 41, 3051;
21. c) H. Östmark, S. Wallin, T. Brinck, P. Carlqvist, R. Claidge, E. Hedlun, L. Yudina, Chem. Phys. Let. 2003, 379, 539;
22. d) P. Carlqvist, H. Östmark, T. Brinck, J. Org. Chem. 2004, 69, 3222;
23. e) S. D. Kunikeev, H. S. Taylor, T. Schroer, R. Haiges, C. J. B. Jones, K. O. Christie, Inorg. Chem. 2006, 45, 437;
24. f) W. W. Wilson, A. Vij, V. Vij, E. Bernhardt, K. O. Christie, Chem. Eur. J. 2003, 9, 2840.
25. a) K. O. Christie, W. W. Wilson, J. A. Sheehy, J. A. Boatz, Angew. Chem. 1999, 111, 2112;
26. Angew. Chem. Int. Ed. 1999, 38, 2004;
27. b) A. Vij, W. W. Wilson, V. Vij, F. S. Tham, K. O. Christie, J. Am. Chem. Soc. 2001, 123, 6308;
28. c) D. A. Dixon, D. Feller, K. O. Christie, W. W. Wilson, A. Vij, H. D. Vij, H. D. B. Brooke, R. M. Olson, M. S. Gordon, J. Am. Chem. Soc. 2004, 126, 834.
29. a.) Y. Mirzaei, B. Twamley, J. M. Shreeve, J. Org. Chem. 2002, 67, 9340;
30. b) R. P. Singh, S. Manandhar, J. M. Shreeve, Tetrahedron Lett. 2002, 43, 9497;
31. c) R. P. Singh, S. Manandhar, J. M. Shreeve, Synthesis 2003, 1579;
32. d) Y. Gao, B. Twamley, J. M. Shreeve, Inorg. Chem. 2004, 43, 3406.
33. a) J.-C. Xiao, J. M. Shreeve, J. Org. Chem. 2005, 70, 3072;
34. b) C. Ye, J.-C. Xiao, B. Twamley, A. D. LaLonde, M. G. Norton, J. M. Shreeve, Eur, J. Org. Chem. 2007, 5095;
35. c) X. Li, Z. Zeng, S. Garg, B. Twamley, J. M. Shreeve, Eur. J. Inorg. Chem. 2008, 3353.
36. a) C. Ye, G. L. Gard, R. W. Winter, R. G. Syvret, B. Twamley, J. M. Shreeve, Org. Lett. 2007, 9, 3841;
37. b) Y. Huang, H. Gao, B. Twamley, J. M. Shreeve, Eur. J. Inorg. Chem. 2008, 2560.
38. a) C. F. Ye, J.-C. Xiao, B. Twamley, J. M. Shreeve, Chem. Commun. 2005, 2750;
39. b) H. Xue, B. Twamley, J. M. Shreeve, J. Mater. Chem. 2005, 15, 3459.
40. nd edn., 2004.
41. a) R. P. Singh, R. D. Verma, D. T. Meshri, J. M. Shreeve, Angew. Chem. 2006, 118, 3664;
42. Angew. Chem. Int. Ed. 2006, 45, 3584-3601;
43. b) V. A. Ostravskii, G. I. Koldobskii, R. E. Trifonov, Tetrazoles. Comprehensive Heterocyclic Chemistry III, Eds. A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Elsevier: Oxford, UK, 2008;
44. c) G. I. Koldobskii, D. S. Soldatenko, E. S. Gerasimova, N. R. Khokhryakova, M. Slicherbinin, V. P. Lebedev, V. A. Ostrovskii, Russ. J. Org. Chem. 1997, 33, 1771.
45. a) R. A. Henry, W. G. Finnegan, J. Am. Chem. Soc. 1954, 76, 923;
46. b) J. M. Keith, J. Org. Chem. 2006, 71, 9540-9543;
47. c) J. J. Shie, J. M. Fang, J. Org. Chem. 2007, 72, 3141.
48. a) K. Karaghiosoff, T. M. Klapötke, P. Mayer, C. Miró Sabaté, A. Penger, J. M. Welch, Inorg. Chem. 2008, 47, 1007;
49. b) T. M. Klapötke, J. Stierstorfer, Helv. Chim. Acta 2007, 90, 2132.
50. a) T. M. Klapötke, P. Mayer, A. Schulz, J. J. Weigand, J. Am. Chem. Soc. 2005, 127, 2032;
51. b) J. C. Gálvez-Ruiz, G. Holl, K. Karaghiosoff, T. M. Klapötke, K. Löhnwitz, P. Mayer, H. Nöth, K. Polborn, C. J. Rohbogner, M. Suter, J. J. Weigand, Inorg. Chem. 2005, 44, 4237.
52. a) R. Stollé, H. Netz, O. Kramer, S. Rothschild, E. Erbe, O. Schick, J. Prakt. Chem. 1933, 755, 1;
53. b) P. N. Gaponik, V. P. Karavai, Khim. Geterotsikl. Soedin. 1984, 1388;
54. c) R. L. Willer, R. A. Henry, J. Org. Chem. 1988, 53, 5371.
55. a) M. von Denffer, T. M. Klapötke, G. Kramer, G. Spieß, J. M. Welch, G. Heeb, Propell., Explos. Pyrot. 2005, 30, 191;
56. b) T. M. Klapötke, C. Miró Sabaté, J. Stierstorfer, Z. Anorg. Allg. Chem. 2008, 634, 1867;
57. c) M. von Denffer, T. M. Klapötke, C. Miró Sabaté, Z. Anorg. Allg. Chem. 2008, 634, 2575.
58. V. Ernst, T. M. Klapötke, J. Stierstorfer, Z. Anorg. Allg. Chem. 2007, 633, 879.
59. T. M. Klapötke, C. Miró Sabaté, Chem. Mater. 2008, 20, 1750.
60. T. M. Klapötke, C. Miró Sabaté, J. M. Welch, Z. Anorg. Allg. Chem. 2008, 634, 857.
61. T. M. Klapötke, C. Miró Sabaté, A. Penger, M. Rusan, J. M. Welch, Eur. J. Inorg. Chem. 2008, 2009, 7, 880.
62. CrysAlis CCD, Version 1.171.27p5 beta; Oxford Diffraction Ltd.
63. CrysAlis RED, Version 1.171.27p5 beta; Oxford. Diffraction Ltd.
64. A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl. Crystallogr. 1993, 26, 343.
65. SHELXS-97, Program for Crystal Structure Solution. G. M. Sheldrick, Institut für Anorganische Chemie der Universität, Tammanstrasse 4, 3400 Göttingen, Germany, 1994.
66. SHELXS-97, Program for Crystal Structure Solution. G. M. Sheldrick, Institut für Anorganische Chemie der Universität, Tammanstrasse 4, 3400 Göttingen, Germany, 1997.
67. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837.
68. PLATON, A Multipurpose Crystallography Tool. A. L. Spek, Utrecht, The Netherlands, 1999.
69. SCALE3 ABSPACK - An Oxford Diffraction program. Oxford Diffraction Ltd., 2005.
70. A copy of the cif files for compound 4 and. 7 can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: int. code(1223)336-1033 E-mail for inquiry: fileserv@ccdc.cam.ac.uk. E-mail for deposition: deposit-@ccdc.cam.ac.uk).
71. D. D. Bray, J. C. White, Acta Crystallogr. Sect. B 1979, 35, 3089.
72. J. Bernstein, R. E. Davis, L. Shimoni, N. Chang, Angew. Chem. 1995, 107, 1555;
73. Angew. Chem. Int. Ed. 1995, 34, 1689.
74. http://www.ccdc.cam.ac.uk/support/documentation/rpluto/TOC.html.
75. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press: New York, 1997.
76. T. M. Klapötke, K. Karaghiosoff, P. Mayer, A. Penger, J. M. Welch, Propell., Explos. Pyrot. 2006, 57, 188.
77. G.-H. Tao, Y. Guo, Y.-H. Joo, B. Twamley, J. M. Shreeve, J. Mater. Chem. 2008, 18, 5524.
78. N. B. Colthup, L. H. Daly, S. E. Wiberley, Introduction to Infrared ana Raman Spectroscopy, Academic Press: Boston, 1990.
79. Gaussian G03W: Gaussian 03, Revision A.1: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Jr. 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. Eliara, 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, 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. Pittsburgh PA, 2003.
80. J. A. Pople, R. Seeger, R. Krishnan, Int. J. Quantum Chem. Symp. 1977, 11, 149.
81. A. K. Rick, T. H. Dunning, J. H. Robert, J. Chem. Phys. 1992, 96, 6796.
82. A. P. Kirk, E. W. David, T. H. Dunning, J. Chem. Phys. 1994, 100, 7410.
83. C. Darwich, T. M. Klapötke, C. Miró Sabaté, Chem. Eur. J. 2008, 14, 5756.
84. a) http://www.bam.de;
85. b) http://www.reichel-partner.de.
86. a) NATO standardization agreement (STANAG) on explosives, impact sensitivity tests, no.4489, Ed. 1, 17 September, 1999;
87. b) NATO standardization agreement. (STANAG) on explosive, friction sensitivity tests, no.4487, Ed. 1, 22 August, 2002.
88. WrWEB-Standardarbeitsanweisung 4-5.1.02, Ermittlung der Explosionsgefährlichkeit, hier der Schlagempfindlichkeit mit dem Fallhammer, 8 November, 2002.
89. Impact: Insensitive >40 J, less sensitive ≥ 35 J, sensitive ≥ 4 J, very sensitive ≤ 3 J; friction: Insensitive >360 N, less sensitive = 360 N, sensitive < 360 N; >80 N, very sensitive ≤ 80 N, extreme sensitive ≤ ION; According to the UN Recommendations on the Transport of Dangerous Goods (+) indicates: not safe for transport.
90. M. Sućeska, Propeli., Explos. Pyrot. 1991, 16, 197;
91. M. Sućeska, Propell., Explos. Pyrot. 1999, 24, 280.
92. M. J. Kamlet, S. J. Jacobs, J. Chem. Phys. 1968, 48, 23.
93. th edn., 1998.
94. Oxygen balance for a compound with the formula CxHyOzMt:Ω(%) = -1600/MW (2 x + y/2 + t - z); M = metal and MW = molecular weight.
95. NIST Chemistry WebBook, NIST Standard Reference Database Number 69, March 2003, www version: http://webbook.nist-.gov/chemistry.
96. a) A. Hammerl, M. A. Hiskey, G. Holl, T. M. Klapötke, K. Polborn, J. Stierstorfer, J. J. Weigand, Chem. Mater. 2005, 17, 3784-3793;
97. b) T. M. Klapötke, C. Miró Sabaté, Chem. Mater. 2008, 20, 3629.
98. C. Darwich, T. M. Klapötke, C. Miró Sabaté, Propell., Explos. Pyrot. 2008, 33, 336.
99. a) ICT-Thermodynamic Code Windows V. 1.00, Fraunhofer ICT Pfinztal, Germany, 1988;
100. b) http://www1.ict.fraunhofer.de/english/projects/defense/ictcode.html.
101. T. M. Klapötke, C. Miró Sabaté, M. Rusan, Z. Anorg. Allg. Chem. 2008, 634, 688.
102. http://www.perkinelmer.com.
103. a) http://www.jeol.com/tabid/96/Default.aspx;
104. b) http://www.jeolusa.com/Desktop/Modules/Bring2mind/DMX/Download.aspx? EntryId = 331&PortalId = 2&DownloadMethod = attachment;
105. c) http://www.jeoleuro.com/instr/mass/mass.htm.
106. http://www.linseis.net/html en/thermal/dsc/dsc pt10.php.
107. http://www.parrinst.com.