3,6,7-Triamino-[1,2,4]triazolo[4,3-b][1,2,4]triazole: A non-toxic, high-performance energetic building block with excellent stability

Chemistry - A European Journal

Volumn 21, Issue 25, 2015, Pages 9219-9228

  Klapötke, Thomas M ^a   Schmid, Philipp C ^a   Schnell, Simon ^a   Stierstorfer, Jörg ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

cations; crystal structures; energetic materials; nitrogen; triazoles

Indexed keywords

CRYSTAL STRUCTURE; DETONATION; ELECTROSTATIC DEVICES; FRICTION; NITRATES; NITROGEN; POSITIVE IONS; STABILITY; TOXICITY;

DECOMPOSITION TEMPERATURE; DETONATION VELOCITY; GUANIDINIUM CATIONS; HYDROXYLAMMONIUM; MECHANICAL STIMULUS; PHYSICOCHEMICAL PROPERTY; TRIAZOLES; TWO-STEP PROTOCOL;

EXPLOSIVES;

EID: 84930675104     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201500982     Document Type: Article

References (57)

1. J. P. Agrawal, High Energy Materials: Propellants, Explosives and Pyrotechnics, Wiley-VCH, 1 st ed., Weinheim, 2010
2. C. B. Jones, R. Haiges, T. Schroer, K. O. Christe, Angew. Chem. Int. Ed. 2006, 45, 4981-4984
3. Angew. Chem. 2006, 118, 5103-5106
4. R. P. Singh, R. D. Verma, D. T. Meshri, J. M. Shreeve, Angew. Chem. Int. Ed. 2006, 45, 3584-3601
5. Angew. Chem. 2006, 118, 3664-3682
6. J. Zhang, J. M. Shreeve, J. Am. Chem. Soc. 2014, 136, 4437-4445
7. Y. Li, C. Qi, S. Li, H. Zhang, C. Sun, Y. Yu, S. Pang, J. Am. Chem. Soc. 2010, 132, 12172-12173.
8. J. Giles, Nature 2004, 427, 580-581
9. M. B. Talawar, R. Sivabalan, T. Mukundan, H. Muthurajan, A. K. Sikder, B. R. Gandhe, A. Subhananda Rao, J. Hazard. Mater. 2009, 161, 589-607.
10. S. Venkatachalam, G. Santhosh, K. N. Ninan, Propellants Explos. Pyrotech. 2004, 29, 178-187
11. Karl. O. Christe, W. W. Wilson, M. A. Petrie, H. H. Michels, J. C. Bottaro, R. Gilardi, Inorg. Chem. 1996, 35, 5068-5071
12. H. Östmark, A. Helte, T. Carlsson, R. Adolfsson, L. Bodin, C. Eldstäter, H. Edvinsson, J. Lundgreen, H. Örnhed, FOI Technical Report, N-guanylurea dinitramide (FOX-12): properties 2007, FOI-R-2312-SE
13. T. M. Klapötke, P. Mayer, A. Schulz, J. J. Weigand, J. Am. Chem. Soc. 2005, 127, 2032-2033
14. A. Hammerl, M. A. Hiskey, G. Holl, T. M. Klapötke, K. Polborn, J. Stierstorfer, J. J. Weigand, Chem. Mater. 2005, 17, 3784-3793
15. M. Göbel, K. Karaghiosoff, T. M. Klapötke, D. G. Piercey, J. Stierstorfer, J. Am. Chem. Soc. 2010, 132, 17216-17226
16. J. C. Bottaro, M. Petrie, P. E. Penwell, A. L. Dodge, R. Malhotra, NANA/HEDM Technology: Late Stage Exploratory Effort, Report No. A466714; SRI International: Menlo Park, CA, 2003
17. N. Fischer, D. Fischer, T. M. Klapötke, D. G. Piercey, J. Stierstorfer, J. Mater. Chem. 2012, 22, 20418-20422
18. P. F. Pagoria, G. S. Lee, A. R. Mitchell, R. D. Schmidt, Thermochim. Acta 2002, 384, 187-204
19. V. Thottempudi, F. Forohor, D. A. Parrish, J. M. Shreeve, Angew. Chem. Int. Ed. 2012, 51, 9881-9885
20. Angew. Chem. 2012, 124, 10019-10023
21. T. M. Klapötke, P. C. Schmid, S. Schnell, J. Stierstorfer, J. Mater. Chem. A 2015, 3, 2658-2668
22. J. Zhang, D. A. Parrish, J. M. Shreeve, Chem. Asian J. 2014, 9, 2953-2960.
23. R. Wang, H. Xu, Y. Guo, R. Sa, J. M. Shreeve, J. Am. Chem. Soc. 2010, 132, 11904-11905
24. V. Thottempudi, J. M. Shreeve, J. Am. Chem. Soc. 2011, 133, 19982-19992
25. Y. Guo, G. H. Tao, Z. Zeng, H. Gao, J. M. Shreeve, Chem. Eur. J. 2010, 16, 3753-3762.
26. L. Liang, K. Wang, C. Bian, L. Ling, Z. Zhou, Chem. Eur. J. 2013, 19, 14902-14910
27. C. Bian, M. Zhang, C. Li, Z. Zhou, J. Mater. Chem. 2015, 3, 163-169
28. Y.-H. Joo, B. Twamley, S. Garg, J. M. Shreeve, Angew. Chem. Int. Ed. 2008, 47, 6236-6239
29. Angew. Chem. 2008, 120, 6332-6335.
30. K. T. Potts, C. Hirsch, J. Org. Chem. 1968, 33, 143-150.
31. R. C. Centore, S. Fusco, A. Capobianco, V. Piccialli, S. Zaccaria, A. Peluso, Eur. J. Org. Chem. 2013, 3721-3728.
32. CCDC-1045074 (2), 1045070 (4), 1045069 (5), 1045073 (6), 1045071 (8), 1045067 (9), 1045072 (11), 1045068 (12), 1045066 (13), and 1045065 (14) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
33. A. Dippold, T. M. Klapötke, Chem. Eur. J. 2012, 18, 16742-16753.
34. T. M. Klapötke, P. Mayer, C. M. Sabaté, J. M. Welch, N. Wiegand, Inorg. Chem. 2008, 47, 6014-6027.
35. A. Katrusiak, Acta Crystallogr. Sect. C 1994, 50, 1161-1163.
36. A. Rheingold, J. Cronin, T. Brill, Acta Crystallogr. Sect. C 1987, 43, 402-404.
37. N. Fischer, T. M. Klapötke, M. Reymann, J. Stierstorfer, Eur. J. Inorg. Chem. 2013, 2167-2180.
38. D. Fischer, T. M. Klapötke, J. Stierstorfer, Angew. Chem. Int. Ed. 2014, 53, 8172-8175
39. Angew. Chem. 2014, 126, 8311-8314.
40. D. Fischer, private communication.
41. T. M. Klapötke, J. Stierstorfer, A. Wallek, Chem. Mater. 2008, 20, 4519-4530.
42. J. Lundgren, R. Liminga, Acta Crystallogr. Sect. B 1979, 35, 1023-1027.
43. B. Dickens, Acta Crystallogr. Sect. B 1969, 25, 1875-1882.
44. H. Gao, C. Ye, C. Piekarski, C. M. Piekarski, J. M. Shreeve, J. Phys. Chem. C 2007, 111, 10718-10731.
45. A. Hammerl, G. Holl, M. Kaiser, T. M. Klapötke, P. Mayer, H. Nöth, H. Piotrowski, M. Sluter, Z. Naturforsch. Sect. B 2001, 56, 857-870.
46. N. Fischer, K. Hüll, T. M. Klapötke, J. Stierstorfer, G. Laus, M. Hummel, Dalton Trans. 2012, 41, 11201-11211.
47. D. Fischer, T. M. Klapötke, D. G. Piercey, J. Stierstorfer, Chem. Eur. J. 2013, 19, 4602-4613.
48. J. W. Ochterski, G. A. Petersson, J. A. Montgomery Jr., J. Chem. Phys. 1996, 104, 2598
49. J. A. Montgomery Jr., M. J. Frisch, J. W. Ochterski, G. A. Petersson, J. Chem. Phys. 2000, 112, 6532
50. M. Hesse, H. Meier, B. Zeeh, Spektroskopische Methoden in der Organischen Chemie, 7 th ed., Thieme, Stuttgart, New York, 2005
51. G. Socrates, Infrared and Raman Characteristic Group Frequencies: Tables and Charts, 3 rd ed., John Wiley & Sons, Chichester, 2004.
52. Y. Murtim, R. Agnihotri, D. Pathak, Am. J. Chem. 2012, 1, 42-46.
53. M. Sucëska, EXPLO5-V6.02 program, Brodarski Institute, Zagreb, Croatia, 2014.
54. Muhamed Sucëska, private communication.
55. C. Xue, J. Sun, B. Kang, Y. Liu, X. Liu, G. Song, Q. Xue, Propellants Explos. Pyrotech. 2010, 35, 333-338.
56. J. Köhler, Explosivstoffe, 9 th ed., Wiley-VCH, New York, 1998, 166.
57. A. Hammerl, T. M. Klapötke, H. Nöth, M. Warchhold, Inorg. Chem. 2001, 40, 3570-3575.