Salts of 1H-tetrazole - Synthesis, characterization and properties

Zeitschrift fur Anorganische und Allgemeine Chemie

Volumn 634, Issue 10, 2008, Pages 1711-1723

  Klapötke, Thomas M ^a   Stein, Marco ^a   Stierstorfer, Jörg ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Calorimetry; Crystal structures; DSC; Energetic Materials; Metal salts; Tetrazoles

Indexed keywords

EID: 53849119485     PISSN: 00442313     EISSN: 15213749     Source Type: Journal    
DOI: 10.1002/zaac.200800139     Document Type: Article

References (59)

1. a) E. Makino, N. Iwasaki, N. Yagi, H. Kato, Y. Ito, H. Azuma, Chem. Pharm. Bull. 1990, 38, 201;
2. b) C. V. Reddy Sastry, Ind. J. Chem. 1990, 29B, 396;
3. c) C. T. Alabaster, J. Med. Chem. 1989, 32, 575;
4. d) M. Uchida, M. Komatsu, S. Morita, T. Kanbe, K. Nagakawa, Chem. Parm. Bull. 1989, 37, 322.
5. M. Friedrich, J. C. Gálvez-Ruiz, T. M. Klapötke, P. Mayer, B. Weber, J. J. Weigand, Inorg. Chem. 2005, 44(22), 8044.
6. a) A. Hammerl, M. A. Hiskey, G. Holl, T. M. Klapötke, K. Polborn, J. Stierstorfer, J. J. Weigand, Chem. Mat. 2005, 17, 3784-3793;
7. b) A. Hammerl, G. Holl, T. M. Klapötke, P. Mayer, H. Nöth, H. Piotrowski, M. Warchhold, Eur. J. Inorg. Chem. 2002, 4, 834-845.
8. a) J. Köhler, R. Mayer, Explosivstoffe, VCH Verlagsgesellschaft, Weinheim, 9. Aufl., 1998, 1;
9. b) R. P. Singh, R. D. Verma, D. T. Meshri, J. M. Shreeve, Angew. Chem. Int. Ed. 2006, 45(22), 3584-3601.
10. F. R. Benson, Chem. Rev. 1947, 41, 1-61.
11. a) M. Roche, L. Pujal, Bull. Soc. Chim. 1969, 1097;
12. b) M. J. S. Dewar, G. J. Gleicher, J. Org. Phys. 1966, 44, 423.
13. K. A.-Jensen, A. Friedinger, Kgl. Danske Videnskab. Selskab. Mat.-Fys. Medd. 1943, 20, 1.
14. a) R. Bronisz, Inorg. Chim. Acta 2002, 340, 215-220;
15. b) F. Jiang, P. R. China. Faming Zhuanli Shenqing Gongkai Shuomingshu, 1993, CN92-108636, 19921117.
16. J. S. Mihina, R. M. Herbst, J. Org. Chem. 1950, 15, 1082.
17. A. Catino, Ann. Chim. 1966, 56, 1332.
18. W. S. McEwan, M. W. Rigg, J. Am. Chem. Soc. 1951, 76, 4725-4727.
19. T. M. Klapötke, in Moderne Anorganische Chemie, E. Riedel (Hrsg.), 3. Aufl., Walter de Gruyter, Berlin, New York, 2007, 99-104.
20. a) H. Feuer, A. T. Nielsen, Nitro Compounds, VCH, New York, 1990;
21. b) A. T. Nielsen, Nitrocarbons; VCH, New York, 1995.
22. R. S. Hamilton, A. J. Sanderson, R. B. Wardle, K. F. Warner, International Annual Conference of ICT 2000, 31st (Energetic Materials), 21/1-21/8.
23. K. Karaghiosoff, T. M. Klapötke, A. Michailowski, G. Holl, Acta Crystallogr. 2002, C58, 580.
24. M.-X. Zhang, P. E. Eaton, R. Gilardi, Angew. Chem. 2000, 112, 422;
25. Angew. Chem. Int. Ed. 2000, 39, 401.
26. CRYSALIS CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CRYSALIS171 .NET), (compiled Apr 1 2005,17:53:34).
27. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)(compiled Apr 1 2005,17:53:34).
28. SIR-92, 1993, A program for crystal structure solution, A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, J. Appl. Cryst. 26, 343.
29. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
30. G. M. Sheldrick SHELXS-97, Program for Crystal Structure Solution, University of Göttingen (Germany), 1997.
31. G. M. Sheldrick, SHELXL-97. Program for the Refinement of Crystal Structures. University of Göttingen (Germany), 1997.
32. A. L. Spek, PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 1999.
33. SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd.
34. Crystallographic data for the structure(s) have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: int.code (1223)336-033; e-mail for inquiry: fileserv@ccdc.cam.ac. uk; e-mail for deposition: deposit-@ccdc.cam.ac.uk).
35. A. M. Astakhov, A. D. Vasiliev, M. S. Molokeey, A. M. Sirotinin, L. A. Kruglyakova, R. S. Stepanov, J. Struct. Chem. (Translation of Zhurnal Strukturnoi Khimii) 2004, 45(1), 175-180.
36. H. A. Laub, T. M. Klapötke, J. Stierstorfer, Propellants, Explos. Pyrotech. 2008, in press.
37. A. D. Vasiliev, A. M. Astakhov, A. A. Nefedov, R. S. Stepanov, J. Struct. Chem. (Translation of Zhurnal Strukturnoi Khimii) 2003, 44(2), 322-325.
38. J. H. Bryden, Acta Crystallogr. 1958, 11, 31-37.
39. E. A. Goiko, N. V. Grigor'eva, N. V. Margolis, A. A. Mel'nikov, T. K. Strochkina, I. V. Tselinskii, J. Struct. Chem. (Translation of Zhurnal Strukturnoi Khimii) 1980, 21(5), 177-80.
40. N. Wiberg, in Lehrbuch der Anorganischen Chemie / Holleman-Wiberg, 101. Ed., de Gruyter, Berlin, 1995, p. 1842.
41. M. Alcami, O. Mo, M. Yanez, J. Phys. Chem. 1989, 93, 3929-3936.
42. G. J. Palenik, Acta Crystallogr. 1963, 16, 596-600.
43. A. Hammerl, G. Holl, T. M. Klapötke, P. Mayer, H. Noth, H. Piotrowski, M. Warchhold, Eur. J. Inorg. Chem. 2002, 4, 834-845.
44. H. P. H. Arp, A. Decken, J. Passmore, D. J. Wood, Preparation, Inorg. Chem. 2000, 39(9), 1840-1848.
45. B. C. Tappan, C. D. Incarvito, A. L. Rheingold, T. B. Brill, Thermochim. Acta 2002, 384(1-2), 113-120.
46. O. A. Ivanshkevich, P. N. Gaponik, N. I. Sushko, V. A. Krasitskii, Zh. Prikl. Spektrosk. 1994, 61, 45-49.
47. 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, 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, 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, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2003.
48. http://www.linseis.com
49. Parr 1356 Isoperibol Bomb Calorimeter, Operating Instruction Manual No. 369M, Parr Instrument Company, Illinois (USA), http://www.parrinst.de/.
50. N. Wiberg, in Lehrbuch der Anorganischen Chemie / Holleman-Wiberg, 101. Ed., de Gruyter, Berlin, 1995, p. 51.
51. N. Wiberg, in Lehrbuch der Anorganischen Chemie / Holleman-Wiberg, 101. Ed., de Gruyter, Berlin, 1995, p. 141.
52. a) N. Wiberg, in Lehrbuch der Anorganischen Chemie / Holleman-Wiberg, 101. Ed., de Gruyter, Berlin, 1995, pp. 250, 859 and 1176;
53. b) http://webbook.nist.gov/chemistry/
54. a) M. Sućeska, Test Methods for Explosives, Springer, New York, 1995, p. 21 (impact), p. 27 (friction);
55. b) http://www.bam.de/.
56. T. M. Klapötke, C. M. Rienäcker, Propellants, Explos., Pyrotech. 2001, 26, 43.
57. Impact: Insensitive > 40 J, less sensitive ≥ 35 J, sensitive ≥ 4, very sensitive ≤ 3 J; friction:Insensitive > 360 N, less sensitive = 360 N, sensitive < 360 N a. > 80 N, very sensitive ≤ 80 N, extreme sensitive ;0k 10 N; According to the UN Recommendations on the Transport of Dangerous Goods (+) indicates: not safe for transport.
58. R. Goddard, O. Heinemann, C. Kruger, Acta Crystallogr. 1997, C53, 590.
59. W. S. McEwan, M. W. Rigg, J. Am. Chem. Soc. 1951, 73, 4725.