A study of dinitro-bis-1,2,4-triazole-1,1′-diol and derivatives: Design of high-performance insensitive energetic materials by the introduction of n-oxides

Journal of the American Chemical Society

Volumn 135, Issue 26, 2013, Pages 9931-9938

  Dippold, Alexander A ^a   Klapötke, Thomas M ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,2 ,4-TRIAZOLE DERIVATIVES; CORRESPONDING COMPOUNDS; INSENSITIVE ENERGETIC MATERIALS; INTERMOLECULAR INTERACTIONS; SPECTROSCOPIC CHARACTERIZATION; STANDARD ENTHALPIES OF FORMATION; STRUCTURAL CHARACTERISTICS; SYNTHESIS AND CHARACTERIZATIONS;

THERMODYNAMIC STABILITY; X RAY CRYSTALLOGRAPHY;

NITROGEN COMPOUNDS;

NITROGEN OXIDE; SODIUM PEROXIDE; TRIAZOLE DERIVATIVE;

ARTICLE; ENTHALPY; HEAT; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; THERMOSTABILITY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDES; THERMODYNAMICS; TRIAZOLES;

EID: 84879766561     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja404164j     Document Type: Article

References (59)

1. Badgujar, D. M.; Talawar, M. B.; Asthana, S. N.; Mahulikar, P. P. J. Hazard. Mater. 2008, 151, 289
2. Klapötke, T. Chemistry of high-energy materials; 2 nd ed.; de Gruyter: Berlin, 2012.
3. Pagoria, P. F.; Lee, G. S.; Mitchell, A. R.; Schmidt, R. D. Thermochim. Acta 2002, 384, 187
4. Singh, R. P.; Verma, R. D.; Meshri, D. T.; Shreeve, J. M. Angew. Chem., Int. Ed. 2006, 45, 3584
5. Sabate, C. M.; Klapötke, T. M. In New Trends in Research of Energetic Materials, Proceedings of the 12th Seminar; University of Pardubice: Czech Republic, 2009, p 172.
6. Yang, S.; Xu, S.; Huang, H.; Zhang, W.; Zhang, X. Prog. Chem. 2008, 20, 526
7. Talawar, M. B.; Sivabalan, R.; Mukundan, T.; Muthurajan, H.; Sikder, A. K.; Gandhe, B. R.; Rao, A. S. J. Hazard. Mater. 2009, 161, 589
8. Klapötke, T. M.; Stierstorfer, J.; Wallek, A. U. Chem. Mater. 2008, 20, 4519
9. Klapötke, T. M.; Sabate, C. M. Chem. Mater. 2008, 20, 3629
10. Chavez, D. E.; Hiskey, M. A.; Naud, D. L. Prop. Explos. Pyrot. 2004, 29, 209
11. Huang, Y.; Gao, H.; Twamley, B.; Shreeve, J. M. Eur. J. Inorg. Chem. 2008, 2560
12. Gao, H.; Shreeve, J. M. Chem. Rev. 2011, 111, 7377
13. High energy density materials; Klapötke, T. M., Ed.; Springer-Verlag: Berlin, 2007.
14. Fischer, N.; Izsák, D.; Klapötke, T. M.; Rappenglück, S.; Stierstorfer, J. Chem.-Eur. J. 2012, 18, 4051
15. Fischer, N.; Klapötke, T. M.; Peters, K.; Rusan, M.; Stierstorfer, J. Z. Anorg. Allg. Chem. 2011, 637, 1693
16. Guo, Y.; Tao, G.-H.; Zeng, Z.; Gao, H.; Parrish, D. A.; Shreeve, J. n. M. Chem.-Eur. J. 2010, 16, 3753
17. Oliveri-Mandala, E.; Passalacqua, T. Gazz. Chim. Ital. 1914, 43, 465
18. Chavez, D. E.; Hiskey, M. A.; Naud, D. L. J. Pyrotech. 1999, 17
19. Metelkina, E. L.; Novikova, T. A.; Berdonosova, S. N.; Berdonosov, D. Y.; Grineva, V. S. Russ. J. Org. Chem. 2004, 40, 1412
20. Metelkina, E. L.; Novikova, T. A.; Berdonosova, S. N.; Berdonosov, D. Y. Russ. J. Org. Chem. 2005, 41, 440
21. Metelkina, E.; Novikova, T. Russ. J. Org. Chem. 2004, 40, 1737
22. Astachov, A. M.; Revenko, V. A.; Kruglyakova, L. A.; Buka, E. S. In New Trends in Research of Energetic Materials, Proceedings of the 10th Seminar; University of Pardubice: Czech Republic, 2007, p 505.
23. Astachov, A. M.; Revenko, V. A.; Buka, E. S. In New Trends in Research of Energetic Materials, Proceedings of the 12th Seminar; University of Pardubice: Czech Republic, 2009, p 396.
24. Wang, R.; Xu, H.; Guo, Y.; Sa, R.; Shreeve, J. M. J. Am. Chem. Soc. 2010, 132, 11904
25. Serov, Y. V.; Pevzner, M. S.; Kofman, T. P.; Tselinskii, I. V. Russ. J. Org. Chem. 1990, 26, 773
26. Bagal, L. I.; Pevzner, M. S.; Frolov, A. N.; Sheludyakova, N. I. Chem. Heterocycl. Compd. 1970, 6, 240
27. Dippold, A. A.; Klapötke, T. M.; Winter, N. Eur. J. Inorg. Chem. 2012, 2012, 3474
28. Rong, D.; Phillips, V. A.; Rubio, R. S.; Castro, M. A.; Wheelhouse, R. T. Tetrahedron Lett. 2008, 49, 6933
29. Klapötke, T. M.; Piercey, D. G.; Stierstorfer, J. Chem.-Eur. J. 2011, 17, 13068
30. Harel, T.; Rozen, S. J. Org. Chem. 2010, 75, 3141
31. Molchanovaa, M. S.; Pivinaa, T. S.; Arnautovab, E. A.; Zefirovb, N. S. J. Mol. Struct. THEOCHEM 1999, 465, 11
32. Goebel, M.; Karaghiosoff, K.; Klapötke, T. M.; Piercey, D. G.; Stierstorfer, J. J. Am. Chem. Soc. 2010, 132, 17216
33. Singh, H.; Mukherjee, U.; Saini, R. S. J. Energ. Mater. 2012, 30, 265
34. Fischer, N.; Fischer, D.; Klapötke, T. M.; Piercey, D. G.; Stierstorfer, J. J. Mater. Chem. 2012, 22, 20418
35. Göbel, M.; Karaghiosoff, K.; Klapötke, T. M.; Piercey, D. G.; Stierstorfer, J. J. Am. Chem. Soc. 2010, 132, 17216
36. Neubauer, H.-J.; Kardoff, U.; Leyendecker, J.; Baus, U.; Künast, C.; Hofmeister, P.; Krieg, W.; Kristgen, R.; Reuther, W.; AG, B. U.S. Patent US5120756, 1992.
37. Begtrup, M.; Vedso, P. J. Chem. Soc. Perk. T. 1 1995, 0, 243
38. Petrie, M. A.; Koolpe, G.; Malhotra, R.; Penwell, P. SRI Project No. P18608 Final report 2012, 7
39. Dippold, A. A.; Klapötke, T. M. Chem.-Eur. J. 2012, 18, 16742
40. Klapötke, T. M.; Piercey, D. G.; Stierstorfer, J. Chem.-Eur. J. 2011, 17, 13068
41. Dippold, A. A.; Klapötke, T. M.; Martin, F. A.; Wiedbrauk, S. Eur. J. Inorg. Chem. 2012, 2012, 2429
42. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Gaussian, Inc.: Wallingford, CT, 2009.
43. Bondi, A. J. Phys. Chem. 1964, 68, 441
44. Nikitina, E. V.; Starova, G. L.; Frank-Kamenetskaya, O. V.; Pevzner, M. S. Kristallografiya 1982, 27, 485
45. Sućeska, M. EXPLO5.5 program; Zagreb, Croatia, 2010.
46. Meyer, R.; Köhler, J.; Homburg, A. Explosives; 6 th ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2007.
47. NATO standardization agreement (STANAG) on explosives and impact tests, no.4489, 1 st ed.; NATO Standardization Agency: Brussels, 1999.
48. WIWEB-Standardarbeitsanweisung 4-5.1.02, Determination of explosions: the impact sensitivity with the monkeys. Weir Research Institute for Materials: Erding, Germany, Nov. 08, 2002.
49. Bundesanstalt für Materalforschung, http://www.bam.de.
50. NATO standardization agreement (STANAG) on explosives, friction tests, no.4487, 1 st ed., NATO Standardization Agency: Brussels, 2002.
51. WIWEB-Standardarbeitsanweisung 4-5.1.03, Determination of explosions: the friction sensitivity with the grinding apparatus. Weir Research Institute for Materials: Erding, Germany, Nov. 08, 2002.
52. NATO standardization agreement (STANAG) on explosives, electrostatic discharge sensitivity tests, no.4490, 1 st ed., NATO Standardization Agency: Brussels, 2001.
53. CrysAlisPro 1.171.36.21; Agilent Technologies: Santa Clara, CA, 2012.
54. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Cryst. 1999, 32, 115-119
55. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen; Göttingen, Germany, 1997.
56. Spek, A. L. Platon, A Multipurpose Crystallographic Tool, Utrecht University: Utrecht, The Netherlands, 2012.
57. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837
58. http://checkcif.iucr.org/
59. Macrae, C. F.; Edgington, P.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Crystallogr. 2006, 39, 565