Synthesis and reactivity of an unexpected highly sensitive 1-carboxymethyl-3-diazonio-5-nitrimino-1,2,4-triazole

New Journal of Chemistry

Volumn 36, Issue 7, 2012, Pages 1463-1468

  Klapötke, Thomas M ^a   Nordheider, Andreas ^a   Stierstorfer, Jörg ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 CARBOXYMETHYL 3 DIAZONIO 5 NITRIMINO 1,2,4 TRIAZOLE; AMPHOLYTE; DIAZONIUM COMPOUND; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NITRATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RAMAN SPECTROMETRY; TEMPERATURE; X RAY DIFFRACTION;

EID: 84862733192     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/c2nj40044h     Document Type: Article

References (41)

1. J. C. Oxley, J. L. Smith, E. Resende, E. Pearce and T. Chamberlain, J. Forensic Sci., 2003, 48, 1-9.
2. (a) C. A. Heller, S. R. Greni and E. D. Erickson, Anal. Chem., 1982, 54, 286-289;
3. (b) Y. Zhang, W. R. Seitz and C. L. Grant, Anal. Chim. Acta, 1989, 217, 217-227;
4. (c) S. Stevanovic and M. Mitrovic, Int. J. Environ. Anal. Chem., 1990, 40, 69-76;
5. (d) T. F. Jenkins and M. E. Walsh, Talanta, 1992, 39, 419-428;
6. (e) R. T. Medary, Anal. Chim. Acta, 1992, 258, 341-346;
7. (f) D. Royds, S. W. Lewis and A. M. Taylor, Talanta, 2005, 67, 262-268;
8. (g) J. Almog, J. Forensic Sci., 2006, 51, 1228-1234.
9. R. G. Smith, N. D'Souza and S. Nicklin, Analyst, 2008, 133, 571-584.
10. Selected papers for the Sixth World Congress on Biosensors, Biosens. Bioelectron., 2001, 1166, 609-1142.
11. K. Y. Lee, L. B. Chapman and M. D. Coburn, J. Energ. Mater., 1987, 5, 27.
12. E. Garcia and K.-Y. Lee, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1992, 48, 1682-1683.
13. F. Einberg, J. Org. Chem., 1970, 35, 3978-3980.
14. CrysAlisPro Oxford Diffraction Ltd., Version 171.33.41, 2009.
15. SIR-92, 1993, A program for crystal structure solution, A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl. Crystallogr., 1993, 26, 343.
16. G. M. Sheldrick SHELXS-97, Program for Crystal Structure Solution, Universität Göttingen, 1997.
17. A. L. Spek, PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 1998.
18. L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.
19. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (CrysAlisPro Oxford Diffraction Ltd., Version 171.33.41, 2009).
20. K. R. Tarantik, dissertation, Ludwig-Maximilian University, Munich, 2010.
21. J. Glinka, D. Fiscus, C. B. Rao and H. Shechter, Tetrahedron Lett., 1987, 28, 3221-3224.
22. S. D. Stepanov and M. S. Pevzner, Zh. Org. Khim., 1989, 25, 2013.
23. (a) G. Daidone, B. Maggio, M. V. Raimondi, G. Bombieri, N. Marchini and R. Artali, Heterocycles, 2005, 65, 2753;
24. (b) X.-M. Zou, F.-Z. Hu and H.-Z. Yang, Chin. J. Struct. Chem., 2004, 23, 149;
25. (c) I. Leban, B. Stanovnik and M. Tisler, Acta Crystallogr., 1978, B34, 293;
26. (d) A. F. Cameron, N. J. Hair and D. G. Morris, J. Chem. Soc., Perkin Trans. 1, 1972, 1331.
27. S. Bräse, C. Gil, K. Knepper and V. Zimmermann, Angew. Chem., 2005, 117, 5320-5374.
28. M. Hesse, H. Meier and B. Zeeh, Spektroskopische Methoden in der organischen Chemie, Thieme Verlag, Stuttgart, 7 edn, 2005.
29. M. Sućeska, Test Methods for Explosives, Springer, New York, 1995, p. 21 (impact), p 27 (friction).
30. (a) http://www.reichel-partner.de;
31. (b) www.bam.de.
32. OZM research, Czech Republic, http:// www.ozm.cz/testing-instruments/ small-scale-electrostatic-discharge-tester.htm.
33. Test methods according to the UN Recommendations on the Transport of Dangerous Goods, Manual of Tests and Criteria, fourth revised edition, United Nations Publication, New York and Geneva 2003, 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 a. > 80N, very sensitive ≤80 N, extremely sensitive ≤10 N.
34. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M.Hada, M. Ehara, K. Toyota,R.Fukuda, J. Hasegawa,M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, 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, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Revision A.1, Gaussian Inc., Wallingford, CT, 2009.
35. GaussView, Version 5, Roy Dennington, Todd Keith and John Millam, Semichem Inc., Shawnee Mission KS, 2009.
36. B. M. Rice and J. J. Hare, J. Phys. Chem., 2002, 106A, 1770. 27
37. (a) P. Politzer, J. S. Murray, J. M. Seminario, P. Lane, M. E. Grice and M. C. Concha, J. Mol. Struct., 2001, 573, 1;
38. (b) J. S. Murray, P. Lane and P. Politzer, Mol. Phys., 1995, 85, 1.
39. Linseis GmbH, Germany, http://www.linseis.com, DSC calibrated with pure indium and zinc; measurements of 1-2 mg of the compounds in pressed Al-container, containing a hole (0.1 mm) for the gas release in a continuous nitrogen flow.
40. N. Fischer, T. M. Klapötke and J. Stierstorfer, J. Energ. Mater., 2011, 29, 61-74.
41. T. Altenburg, T. M. Klapötke, A. Penger and J. Stierstorfer, Z. Anorg. Allg. Chem., 2010, 636, 463-471.