4-(1-Amino-5-aminotetrazolyl)methyleneimino-3-methylfuroxan and its derivatives: Synthesis, characterization, and energetic properties

European Journal of Inorganic Chemistry

Volumn , Issue 7, 2014, Pages 1231-1238

  Tang, Yongxing ^a   Yang, Hongwei ^a   Shen, Jianhua ^a   Wu, Bo ^a   Ju, Xuehai ^a   Lu, Chunxu ^a   Cheng, Guangbin ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Density functional calculations; Energetic materials; Nitrogen heterocycles; Structure elucidation

Indexed keywords

DETONATION; NITROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SALTS; SINGLE CRYSTALS; THERMODYNAMIC STABILITY; X RAY DIFFRACTION ANALYSIS; CONDENSATION REACTIONS;

DENSITY-FUNCTIONAL CALCULATIONS; DERIVATIVE SYNTHESIS; ENERGETIC PROPERTIES; HEATS OF FORMATION; HIGHER YIELD; HNO 3; NITROGEN HETEROCYCLES; NITROGEN-RICH SALT; STRUCTURE ELUCIDATION; X-RAY DIFFRACTION STUDIES; 3-AMINO-1;

CONDENSATION REACTIONS; DENSITY FUNCTIONAL THEORY;

EID: 84897678872     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201301363     Document Type: Article

References (63)

1. Y. Q. Zhang, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. 2013, 1, 585-593.
2. N. Fischer, D. Fischer, T. M. Klapötke, D. G. Piercey, J. Stierstorfer, J. Mater. Chem. 2012, 22, 20418-20422.
3. G. H. Tao, Y. Guo, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. 2010, 20, 2999-3005.
4. A. A. Dippold, T. M. Klapötke, J. Am. Chem. Soc. 2013, 135, 9931-9938.
5. Y.-H. Joo, J. M. Shreeve, Angew. Chem. 2010, 122, 7478; Angew. Chem. Int. Ed. 2010, 49, 7320-7323.
6. Y.-H. Joo, J. M. Shreeve, J. Am. Chem. Soc. 2010, 132, 15081-15090.
7. L. V. Batog, L. S. Konstantinova, O. V. Lebedev, L. I. Khmel'nitskii, Mendeleev Commun. 1996, 6, 193-195.
8. H. F. Huang, Z. M. Zhou, L. X. Liang, J. H. Song, K. Wang, D. Cao, W. W. Sun, C. M. Bian, M. Xue, Z. Anorg. Allg. Chem. 2012, 638, 392-400.
9. P. W. Leonard, D. E. Chavez, P. F. Pagoria, D. L. Parrish, Propellants Explos. Pyrotech. 2011, 36, 233-239.
10. H. V. Huynh, M. A. Hiskey, D. E. Chavez, D. L. Naud, R. D. Gilardi, J. Am. Chem. Soc. 2005, 127, 12537-12543.
11. A. Saikia, R. Sivabalan, B. G. Polke, G. M. Gore, A. Singh, A. S. Rao, A. K. Sikder, J. Hazard. Mater. 2009, 170, 306-313.
12. M. Göbel, T. M. Klapötke, Adv. Funct. Mater. 2009, 19, 347-365.
13. J. Kerth, S. Löbbecke, Propellants Explos. Pyrotech. 2002, 27, 111-118.
14. M. Göbel, K. Karaghiosoff, T. M. Klapötke, D. G. Piercey, J. Stierstorfer, J. Am. Chem. Soc. 2010, 132, 17216-17226.
15. N. Fischer, D. Izsak, T. M. Klapötke, J. Stierstorfer, Chem. Eur. J. 2013, 19, 8948-8957.
16. Y.-H. Joo, J. M. Shreeve, Angew. Chem. 2009, 121, 572; Angew. Chem. Int. Ed. 2009, 48, 564-567.
17. A. A. Dippold, T. M. Klapötke, J. Am. Chem. Soc. 2013, 135, 9931-9938.
18. T. M. Klapötke, C. M. Sabate, Eur. J. Inorg. Chem. 2008, 5350-5366.
19. A. A. Dippold, T. M. Klapötke, F. A. Martin, S. Wiedbrauk, Eur. J. Inorg. Chem. 2012, 2429-2443.
20. H. F. Huang, Z. M. Zhou, L. X. Liang, J. H. Song, K. Wang, D. Cao, W. W. Sun, C. M. Bian, M. Xue, Chem. Asian J. 2012, 7, 707-714.
21. L. X. Liang, H. F. Huang, K. Wang, C. M. Bian, J. H. Song, L. M. Ling, F. Q. Zhao, Z. M. Zhou, J. Mater. Chem. 2012, 22, 21954-21964.
22. T. M. Klapötke, F. A. Martin, J. Stierstorfer, Chem. Eur. J. 2012, 18, 1487-1501.
23. J. C. Galvez-Ruiz, G. Holl, K. Karaghiosoff, T. M. Klapötke, K. Lohnwitz, P. Mayer, H. Noth, K. Polborn, C. J. Rohbogner, M. Suter, J. J. Weigand, Inorg. Chem. 2005, 44, 4237-4253.
24. Y.-H. Joo, B. Twamley, S. Garg, J. M. Shreeve, Angew. Chem. 2008, 120, 6332-6335.
25. Y.-H. Joo, B. Twamley, J. M. Shreeve, Chem. Eur. J. 2009, 15, 9097-9104.
26. F. Li, X. M. Cong, Z. M. Du, C. L. He, L. S. Zhao, L. Q. Meng, New J. Chem. 2012, 36, 1953-1956.
27. Y. X. Tang, H. W. Yang, J. H. Shen, B. Wu, X. H. Ju, C. X. Lu, G. B. Cheng, Angew. Chem. Int. Ed. 2013, 52, 4875-4877.
28. V. P. Sinditskii, A. V. Burzhava, A. B. Sheremetev, N. S. Aleksandrova, Propellants Explos. Pyrotech. 2010, 37, 575-580.
29. I. N. Zyuzin, K. Y. Suponitsky, A. B. Sheremetev, J. Heterocycl. Chem. 2012, 49, 561-565.
30. E. G. Francois, D. E. Chavez, M. M. Sandstrom, Propellants Explos. Pyrotech. 2010, 35, 529-534.
31. L. X. Wang, X. L. Tuo, C. H. Yi, H. T. Zou, J. Xu, W. L. Xu, J. Mol. Graphics Modell. 2009, 28, 81-87.
32. J. P. Agrawal, High energy materials, Propellants, Explosives and Pyrotechnics, Wiley-VCH, Weinheim, Germany, 2010, p. 100-102.
33. C. Zhang, THEOCHEM 2006, 765, 77-83.
34. R. Fruttero, B. Ferrarotti, A. Serafino, A. D. Stilo, A. Gosco, J. Heterocycl. Chem. 1989, 26, 1345-1347.
35. P. N. Gaponik, V. P. Karavai, Chem. Heterocycl. Compd. 1984, 20, 1388-1391.
36. L. X. Liang, K. Wang, C. M. Bian, L. M. Ling, Z. M. Zhou, Chem. Eur. J. 2013, 19, 14902-14910.
37. M. J. Kamlet, S. J. Jacobs, J. Chem. Phys. 1968, 48, 23-35.
38. M. J. Kamlet, S. J. Jacobs, J. Chem. Phys. 1968, 48, 36-42.
39. V. Thottempudi, F. Forohor, D. A. Parrish, J. M. Shreeve, Angew. Chem. Int. Ed. 2012, 51, 9881-9885.
40. Y.-H. Joo, H. X. Gao, D. A. Parrish, S. G. Cho, E. M. Goh, J. M. Shreeve, J. Mater. Chem. 2012, 22, 6123-6130.
41. Q. H. Lin, Y. C. Li, Y. Y. Li, Z. Wang, W. Liu, C. Qi, S. P. Pang, J. Mater. Chem. 2012, 22, 666-674.
42. Test methods were performed according to the UN Recommendations on the Transport of Dangerous Goods, Manual of Tests and Criteria, 4th rev. ed., United Nations Publications, New York, 2003; 13.4.2 Test 3, (ii) BAM Fallhammer, p. 75-82.
43. N. Fischer, T. M. Klapötke, M. Reymann, J. Stierstorfer, Eur. J. Inorg. Chem. 2013, 2167-2180.
44. R. Mayer, J. Köhler, A. Homburg, in: Explosives, vol. 5, Wiley-VCH, Weinheim, Germany, 2002.
45. 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, V. Bakken, 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, A. L. G. Liu, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, revision D. 01, Gaussian, Inc., Wallingford CT, 2004.
46. H. D. B. Jenkins, D. Tudeal, L. Glasser, Inorg. Chem. 2002, 41, 2364-2367.
47. APEX2, v. 2010.3-0, Bruker AXS Inc., Madison, 2010.
48. SAINT, v. 7.68A, Bruker AXS Inc., Madison, 2009.
49. XPREP, v. 2008/2, Bruker AXS Inc., Madison, 2008.
50. SADABS, v. 2008/1, Bruker AXS Inc., Madison, 2008.
51. SHELXTL, v. 2008/4, Bruker AXS Inc., Madison, 2008.
52. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
53. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
54. P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213-222.
55. D. R. Lide, CRC Handbook of Chemistry and Physics, 88th, ed. (Internet Version 2008), CRC Press/Taylor and Francis, Boca Raton, 2007-2008.
56. N. Fischer, T. M. Klapötke, J. Stierstorfer, Z. Anorg. Allg. Chem. 2009, 635, 271-281.
57. Y.-H. Joo, J. H. Chung, S. G. Cho, E. M. Goh, New J. Chem. 2013, 37, 1180-1188.
58. G. W. Drake, G. M. Kaplan, T. W. Hawkins, US 2005203578.
59. W. T. Quinlin, D. M. Cates, US 2005165241.
60. A. N. Kost, F. Gents, Zh. Obshch. Khim. 1958, 28, 2773-2779.
61. I. Matulkova, I. Nemec, K. Teubner, P. Nemec, Z. Micka, J. Mol. Struct. 2008, 873, 46-60.
62. G. Sjostedt, L. Gringas, Org. Synth. 1946, 26.
63. X. H. Sun, Y. F. Liu, S. Z. Chen, B. Chen, Y. Q. Jia, Z. F. Zeng, Chin. J. Chem. 2009, 27, 949-952.