The synthesis of di(aminoguanidine) 5-nitroiminotetrazolate: Some diprotic or monoprotic acids as precursors of energetic salts

Chemistry - A European Journal

Volumn 14, Issue 18, 2008, Pages 5596-5603

  Gao, Haixiang ^b   Huang, Yangen ^a   Ye, Chengfeng ^a   Twamley, Brendan ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

^b CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

Ab initio calculations; Energetic compounds; Heats of formation; Nitrogen; Salt formation

Indexed keywords

ACIDS; AMINES; GRAVIMETRIC ANALYSIS; KETONES; SYNTHESIS (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS;

AB INITIO CALCULATIONS; ENERGETIC COMPOUNDS; HEATS OF FORMATION; NITROGEN; SALT FORMATION;

SALTS;

EID: 53849087869     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800238     Document Type: Article

References (73)

1. a) N. R. Badders, C. Wei, A. A. Aldeeb, W. J. Rogers, M. S. Mannan, J. Energ. Mater. 2006, 24, 17-33;
2. b) O. Siri, P. Braunstein. New J. Chem. 2005, 29, 75-79;
3. c) G. Singh, I. P. S. Kapoor, S. M. Mannan, S. K. Tiwari, J. Hazard. Mater. 1999, 68, 155-178.
4. a) R. P. Singh, R. D. Verma, D. T. Meshri, J. M. Shreeve. Angew. Chem. 2006, 118, 3664-3682;
5. Angew. Chem. Int. Ed. 2006, 45, 3584-3601, and references therein;
6. b) R. P. Singh, H. X. Gao, D. T. Meshri, J. M. Shreeve, Struct. Bonding (Berlin) 2007, 125, 35-83;
7. c) T. M. Klapötke, Struct. Bonding (Berlin) 2007, 125, 85-121.
8. a) M.-H. V. Huynh. M. A. Hiskey, E. L. Hartline, D. P. Montoya, R. Gilardi, Angew. Chem. 2004, 116, 5032-5036;
9. Angew. Chem. Int. Ed. 2004, 43, 4924-4928;
10. b) R. Haiges, S. Schneider, T. Schroer, K. O. Chrisle, Angew. Chem. 2004, 116, 5027-5032;
11. Angew. Chem. Int. Ed. 2004, 43, 4919-4924, and references therein;
12. c) G. Drake, US-A 6509473, 2003;
13. d) G. Drake, T. Hawkins. AFOSR Ionic Liquids Workshop, 2002, Dulles, VA;
14. e) G. Drake, AFOSR Ionic Liquids Workshop, 2003, Aberdeen, MD;
15. f) G. Kaplan, G. Drake, K. Tollison, L. Hall, T. Hawkins, J. Heterocycl. Chem. 2005, 42, 19-27;
16. g) G. Drakem, T. W. Hawkins, J. A. Boatz, L. Hall, A. Vij, Propellants Explos. Pyrotech. 2005, 30, 156-163;
17. h) G. W. Drake, T. W. Hawkins, L. A. Hall, J. A. Boatz, A. Brand, Propellants Explos. Pyrotech. 2005, 30, 329-337;
18. i) A. Hammerl, M. A. Hiskey, G. Holl, T. M. Klapölke, K. Polborn, J. Slierstorfer, J. J. Weigand, Chem. Mater. 2005, 17, 3784-3793.
19. a) H. Xue, Y. Gao, B. Twamley, J. M. Shreeve, Chem. Mater. 2005, 17, 191-198;
20. b) H. Xue, S. W. Arritt, B. Twamley, J. M. Shreeve, Inorg. Chem. 2004, 43, 7972-7977;
21. c) Y. Gao, S. W. Arritt, B. Twamley, J. M. Shreeve. Inorg. Chem. 2005, 44, 1704-1712;
22. d) C. F. Ye, J. M. Shreeve, Chem. Commun. 2005, 2570-2572;
23. e) H. Xue, Y. Gao, B. Twamley. J. M. Shreeve, Inorg. Chem. 2005, 44, 5068-5072;
24. f) H. Xue, B. Twamley, J. M. Shreeve, J. Mater. Chem. 2005, 15, 3459-3465;
25. g) H. Xue, Y. Gao, B. Twamley, J. M. Shreeve, Inorg. Chem. 2005, 44, 7009-7013;
26. h) C.-M. Jin, C. F. Ye, C. Piekarski, B. Twamley, J. M. Shreeve. Eur. J. Inorg. Chem. 2005, 18, 3760-3767;
27. i) H. Xue, H. Gao, B. Twamley, J. M. Shreeve, Eur. J. Inorg. Chem. 2006, 15, 2959-2965;
28. j) H. Gao, C. Ye, R. W. Winter, G. L. Gard, M. E. Sitzmann, J. M. Shreeve, Eur. J. Inorg. Chem. 2006, 15, 3221-3226;
29. k) Y. Gao, C. F. Ye, B. Twamley, J. M. Shreeve, Chem. Eur. J. 2006, 12, 9010-9018;
30. l) H. Gao, R. Wang, B. Twamley, M. A. Hiskey, J. M. Shreeve, Chem. Commun. 2006, 4007-4009;
31. m) H. Gao, C. Ye, O. D. Gupta, J.-C. Xiao, M. A. Hiskey, B. Twamley, J. M. Shreeve. Chem. Eur. J. 2007, 13, 3853-3860;
32. n) Y. Huang, H. Gao, B. Twamley, J. M. Shreeve, Eur. J. Inorg. Chem. 2007, 2025-2030;
33. o) Z. Zeng, H. Gao, B. Twamley, J. M. Shreeve, J. Mater. Chem. 2007, 17, 3819-3826;
34. p) H. Xue, H. Gao, B. Twamley, J. M. Shreeve, Chem. Mater. 2007, 19, 1731-1739;
35. q) Y. Guo, H. Gao, B. Twamley, J. M. Shreeve. Adv. Mater. 2007, 19, 2884-2888;
36. r) C. Ye, J. M. Shreeve, J. Phys. Chem. A, 2007, 111, 1456-1461;
37. s) R. Wang, H. Gao, C. Ye, B. Twamley, J. M. Shreeve, Inorg. Chem. 2007, 46, 932-938.
38. a) E. R. Atkinson, J. Am. Chem. Soc. 1951, 73, 4443-4444;
39. b) H. Bredereck, F. Effenberger, H. Franz, M. Hajek, Chem. Ber. 1968, 101, 3062-3069;
40. c) P. N. Simoes, A. T. Portugal, J. A. Campos, Thermochim. Acta 1997, 298, 95-108;
41. d) O. Hidenari, Y. Hiroshi, Jpn. Kokal Tokkyo Koho, JP2000119088, 2000
42. [Chem. Abstr. 2000 132, 295821];
43. e) P. Simoes, L. Pedroso, A. Portugal, P. Carvalheira, J. Campos, Propellants Explos. Pyrotech. 2001, 26, 273-277;
44. f) P. Simoes, L. Pedroso, A. Portugal, I. Plaksin, J. Campos. Propellants Explos. Pyrotech. 2001, 26, 278-283;
45. g) P. N. Simoes, L. M. Pedroso, A. M. Beja, S. M. Matos, M. E. Ramos, A. A. Portugal, J. Phys. Chem. A 2007, 111, 150-158.
46. a) H. Y. Chen, T. L. Zhang, J. G. Zhang, K. B. Yu, J. Chem. Crystallogr. 2006, 36, 181-187;
47. b) H. Takeyoshi, Jpn. Tokkyo Koho, JP19661219, 1969.
48. [Chem. Abstr. 1970 72, 42929].
49. T. P. Kofman, G. Y. Kartseva, M. B. Shcherbinin, Russ. J. Org. Chem. 2002, 38, 1343-1350.
50. a) R. M. Herbst, J. A. Garrison, J. Org. Chem. 1953, 18, 941-945;
51. b) T. M. Klapoetke, J. Stierstorfer, Helv. Chim. Acta 2007, 90, 2132-2150;
52. c) S. N. Semenov, A. Y. Rogachev, S. V. Eliseeva, Y. A. Belousov, A. A. Drozdov, S. I. Troyanov. Polyhedron 2007, 26, 4899-4907.
53. M. Tremblay, Can. J. Chem. 1965, 43, 1230-1232.
54. a) M. W. Schmidt, M. S. Gordon. J. A. Boatz, J. Phys. Chem. A 2005, 109, 7285-7295;
55. b) K. E. Gutowski, R. D. Rogers, D. A. Dixon, J. Phys. Chem. B 2007, 111, 4788-4800;
56. c) K. E. Gulowski, J. D. Holbrey, R. D. Rogers, D. A. Dixon, J. Phys. Chem. B 2005, 109, 23196-23208;
57. d) H. Gao, C. Ye, C. Piekarski, J. M. Shreeve, J. Phys. Chem. C 2007, 111, 10718-10731.
58. a) M. H. Keshavarz, H. R. Pouretedal, A. Semnani, J. Hazard. Mater. 2007, 141, 803-807;
59. b) M. H. Keshavarz, J. Hazard. Mater. 2007, 148, 648-652.
60. R. A. Henry, J. E. De Vries, R. H. Boschan. J. Am. Chem. Soc. 1955, 77, 5693-5695.
61. a) P. Politzer, J. S. Murray, M. E. Grice, P. Sjoberg in Chemistry of Energetic Materials (Eds.: G. A. Olah, D. R. Squire), Academic Press, San Diego, CA, 1991, pp. 77-93;
62. b) J. Köhler, R. Mayer, Explosivstoffe, 9th ed., Wiley-VCH, Weinheim, 1998.
63. a) L. E. Fried, K. R. Glaesemann, W. M. Howard, P. C. Souers, CHEETAH 4.0 User's Manual, Lawrence Livermore National Laboratory. 2004;
64. b) J. P. Lu, Evaluation of the Thermochemicat Code - CHEETAH 2.0 for Modelling Explosives Performance, DSTO-DR-1199, Defence Science and Technology Organization (Australian Government), Edinburgh, 2001.
65. B. C. Tappan, C. D. Incarvito, A. L. Rheingold, T. B. Brill, Thermochim. Acta, 2002, 384, 113-120.
66. Gaussian 03, Revision D.01, 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, 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, J. A. Pople, Gaussian, Inc., Wallingford, CT, 2004.
67. R. G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
68. H. D. B. Jenkins, D. Tudeal, L. Glasser, Inorg. Chem. 2002, 41, 2364-2367.
69. SMART, Ver. 5.632, Bruker AXS, Madison, WI, 2005.
70. SAINTPlus, Ver. 7.23a (Data Reduction and Correction Program), Bruker AXS, Madison, WI, 2004.
71. SADABS. Ver. 2004/1 (Empirical Absorption Correction Program), Bruker AXS Inc., Madison, WI, 2004.
72. SHELXTL, Ver. 6.14 (Structure Determination Software Suite), G. M. Sheldrick, Bruker AXS Inc., Madison, WI, 2004.
73. F. Saczewski, A. Bulakowska, P. Bednarski, R. Grunert, Eur. J. Med. Chem. 2006, 41, 219-225.