Polyamino-substituted guanyl-triazole dinitramide salts with extensive hydrogen bonding: Synthesis and properties as new energetic materials

Chemistry of Materials

Volumn 20, Issue 19, 2008, Pages 6176-6182

  Zeng, Zhuo ^a   Wang, Ruihu ^a   Twamley, Brendan ^a   Parrish, Damon A ^b   Shreeve, JeaN'Ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO GROUPS; AMMONIUM DINITRAMIDE; DETONATION PRESSURES; DINITRAMIDE; DINITRAMIDE ANIONS; ENERGETIC MATERIALS; ENERGETIC SALTS; GUANYLUREA; HIGH DENSITIES; HYDROGEN BONDINGS; POLYAMINO; THEORETICAL CALCULATIONS; THERMAL STABILITIES; TRIAZOLE RUNG;

AMINATION; AMINES; AMMONIUM COMPOUNDS; HYDROGEN; HYDROGEN BONDS; MATERIALS PROPERTIES; ORGANIC POLYMERS; POSITIVE IONS; SALTS; X RAY DIFFRACTION ANALYSIS;

NITROGEN COMPOUNDS;

EID: 54849427699     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm801679a     Document Type: Article

References (57)

1. (a) Luk'yanov, O. A.; Gorelik, V. P.; Tartakovskii, V. A. Russ. Chem. Bull. 1994, 1, 94-97.
2. (b) Shlyapochnikov, V. A.; Cherskaya, N. O.; Luk'yanov, O. A.; Gorelik, V. P.; Tartakovskii, V. A. Russ. Chem. Bull. 1994, 9, 1610-1613.
3. (c) Luk'yanov, O. A.; Anikin, O. V.; Gorelik, V. P.; Tartakovskii, V. A. Russ. Chem. Bull. 1994, 9, 1546-1549.
4. (d) Shlyapochnikov, V. A.; Oleneva, G. I.; Cherskaya, N. O.; Luk'yanov, O. A.; Gorelik, V. P.; Anikin, O. V.; Tartakovskii, V. A. Russ. Chem. Bull. 1995, 8, 1508-1512.
5. (e) Luk'yanov, O. A.; Gorelik, V. P.; Tartakovskii, V. A. Ross. Khim. Zh. 1997, 41, 5-13.
6. (f) Schmitt, R. J.; Bottaro, J. C.; Penwell, P. E.; Ross, D. S. PCT Int. WO9316002, 1993;
7. Chem. Abstr. 1993, 120, 11330.
8. (g) Bottaro, J. C.; Penwell, P. E.; Schmitt, R. J. J. Am. Chem. Soc. 1997, 119, 9405-9410.
9. (a) Christe, K. O.; Wilson, W. W.; Petrie, M. A.; Michels, H. H.; Bottaro, J. C.; Gilardi, R. Inorg. Chem. 1996, 35, 5068-5071.
10. (b) Petrie, M. A.; Sheehy, J. A.: Boatz, J. A.; Rasul, G.; Prakash, G. K. S.; Olah, G. A.; Christe, K. O. J. Am. Chem. Soc. 1997, 119, 8802-8808.
11. (c) Drake, G.; Hawkins, T. W.; Hall, L. A.; Boatz, J. A.; Brand, A. J. Propellants, Explos. Pyrotech. 2005, 30, 329-337.
12. Gilardi, R.; Flippen-Anderson, J.; George, C.; Butcher, R. J. J. Am. Chem. Soc. 1997, 119, 9411-9416.
13. Ang, H.-G.; Fraenk, W.; Karaghiosoff, K.; Klapötke, T. M.; Mayer, P.; Nöth, H.; Sprott, J.; Warchhold, M. Z. Anorg. Allg. Chem. 2002, 628, 2894-2900.
14. Ang, H.-G.; Fraenk, W.; Karaghiosoff, K.; Klapötke, T. M.; Nöth, H.; Sprott, J.; Suter, M.; Vogt, M.; Warchhold, M. Z. Anorg. Allg. Chem. 2002, 628, 2901-2906.
15. Gilardi, R.; Butcher, R. J. J. Chem. Crystallogr. 2002, 32, 477-484.
16. (a) Zhurova, E. A.; Martin, A.; Pinkerton, A. A. J. Am. Chem. Soc. 2002, 124, 8741-8750.
17. (b) Martin, A.; Pinkerton, A. A.; Gilardi, R. D.; Bottaro, J. C. Acta Crystallogr. 1997, B53, 504-512.
18. Östmark, H.; Bemm, U.; Bergman, H.; Langlet, A. Thermochim. Acta 2002, 384, 253-259.
19. (a) Drake, G.; Hawkins, T.; Brand, A.; Hall, L.; Mckay, M. Propellents, Explos. Pyrotech. 2003, 28, 174-180.
20. (b) Drake, G. W. United States Patent 6509473, 2003.
21. (c) Li, H.; Boatz, J. A.; Gordon, M. S. J. Am. Chem. Soc. 2008, 130, 392-393.
22. (a) Klapötke, T. M.; Mayer, P.; Schulz, A.; Weigand, J. J. J. Am. Chem. Soc. 2005, 127, 2032-2033.
23. (b) Fischer, G.; Holl, G.; Klapötke, T. M.; Weigand, J. J. Thermochim. Acta 2005, 437, 168-178.
24. Löbbecke, S.; Krause, H.; Pfei, A. Propellants, Explos. Pyrotech. 1997, 22, 184-188.
25. (a) Xue, H.; Shreeve, J. M. Adv. Mater. 2005, 17, 2142-2146.
26. (b) Ye, C.; Gao, H.; Boatz, J. A.; Drake, G. W.; Twamley, B.; Shreeve, J. M. Angew. Chem., Int. Ed. 2006, 45, 7262-7265.
27. (c) Guo, Y.; Gao, H.; Twamley, B.; Shreeve, J. M. Adv. Mater. 2007, 19, 2884-2888.
28. (d) Zeng, Z.; Gao, H.; Twamley, B.; Shreeve, J. M. J. Mater. Chem. 2007, 17, 3819-3826.
29. (a) Michel, P.; Gerard, M.; Philippe, B. PCT Int. WO2007135297, 2007;
30. Chem. Abstr. 2007, 148, 16892.
31. (b) D'Alello, G. F. United States Patent 2352944, 1944.
32. (c) Zeng, Z.; Hyer, W. S.; Twamley, B.; Shreeve, J. M. Synthesis 2008, 1775-1782.
33. Naito, Y.; Akahoshi, F.; Takeda, S.; Okada, T.; Kajii, M.; Nishimura, H.; Sugiura, M.; Fukaya, C.; Kagitani, Y. J. Med. Chem. 1996, 39, 3019-3029.
34. Zhurova, E. A.; Tsirelson, V. G.; Stash, A. I.; Pinkerton, A. A. J. Am. Chem. Soc. 2002, 124, 4574-4575.
35. Gilardi, R. D.; Butcher, R. J. J. Chem. Crystallogr. 1998, 28, 163-169.
36. (a) Klapötke, T. M.; StierstorferJ. Eur. J. Inorg. Chem. 2008, 4055-4062.
37. (b) Klapötke, T. M.; Stierstorfer, J. Phys. Chem. Chem. Phys. 2008, 10, 4340-4346.
38. Fried, L. E.; Glaesemann, K. R.; Howard, W. M.; Souers, P. C. CHEETAH 4.0 User's Manual; Lawrence Livermore National Laboratory: Livermore, CA, 2004.
39. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
40. Parr, R. G., Yang, W., Eds. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
41. Jenkins, H. D. B.; Tudeal, D.; Glasser, L. Inorg. Chem. 2002, 41, 2364-2367.
42. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. H.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data, Suppl. 1988, 1, 17.
43. Schmidt, M. W.; Gordon, M. S.; Boatz, J. A. J. Phys. Chem. A 2005, 109, 7285-7295.
44. Gao, H.; Ye, C.; Piekarski, C. M.; Shreeve, J. M. J. Phys. Chem. C 2007, 111, 10718-10731.
45. Michels, H. H.; Montgomery, J. A., Jr. J. Phys. Chem. 1993, 97, 6602-6604.
46. Hope, H. Prog. Inorg. Chem. 1994, 41, 1.
47. SMART: v5.625 (7, 9), 2001, and v. 5.632 (8, 10), 2005;
48. Bruker AXS Inc.: Madison, WI.
49. SAINTPlus: SAINT v6.36A. (7, 9), 2002, and v. 7.23a (8, 10), 2004;
50. Bruker AXS Inc.: Madison, WI.
51. XPREP, v6.12; Bruker AXS Inc.: Madison, WI, 2001.
52. SADABS: v2.03 (7, 9), 2000, v.2007/4 (8, 10), 2007;
53. Bruker AXS Inc.: Madison, WI.
54. SHELXTL: v. 6.10 (7, 9), 2000, and v. 6.14 (8, 10), 2004;
55. Bruker AXS Inc., Madison, WI.
56. Sheldrick, G. M. CELL_NOW, 2002.
57. TWINABS, v. 2007/5; Bruker AXS Inc.: Madison, WI, 2007.