Molecular design of 1,2,4,5-tetrazine-based high-energy density materials

Journal of Physical Chemistry A

Volumn 113, Issue 33, 2009, Pages 9404-9412

  Wei, Tao ^a,b   Zhu, Weihua ^a   Zhang, Xiaowen ^a   Li, Yu Fang ^a   Xiao, Heming ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b WENZHOU MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BOND DISSOCIATION ENERGIES; COOH GROUP; DETONATION VELOCITY; HEATS OF FORMATION; HIGH ENERGY DENSITY MATERIALS; MOLECULAR DESIGN; OH GROUP; SEMI-EMPIRICAL METHODS; TETRAZINES; THERMAL STABILITY;

CHEMICAL BONDS; DETONATION; THERMODYNAMIC STABILITY;

DENSITY FUNCTIONAL THEORY;

SINGLE HETEROCYCLIC RINGS; TETRAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG DESIGN; HEAT; PRESSURE; QUANTUM THEORY; REPRODUCIBILITY; THERMODYNAMICS;

DRUG DESIGN; HETEROCYCLIC COMPOUNDS, 1-RING; HOT TEMPERATURE; PRESSURE; QUANTUM THEORY; REPRODUCIBILITY OF RESULTS; TETRAZOLES; THERMODYNAMICS;

EID: 70349194929     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp902295v     Document Type: Article

References (58)

1. Fried, L. E.; Manaa, M. R.; Pagoria, P. F.; Simpson, R. L. Annu. Rev. Mater. Res. 2001, 31, 291.
2. Strout, D. L. J. Phys. Chem. A 2004, 108, 10911.
3. Nguyen, M. T. Coord. Chem. Rev. 2003, 244, 93.
4. Xu, X. J.; Xiao, H. M.; Ju, X. H.; Gong, X. D.; Zhu, W. H. J. Phys. Chem. A 2006, 110, 5929.
5. Rice, B. M.; Byrd, E. F. C.; Mattson, W. D. Struct. Bonding (Berlin) 2007, 125, 85.
6. Klapötke, T. M. Struct. Bonding (Berlin) 2007, 125, 153.
7. Benson, F. R. The High Nitrogen Compounds; Wiley-Interscience: New York, 1984.
8. Chavez, D. E.; Hiskey, M. A.; Gilardi, R. D. Angew. Chem., Int. Ed. 2000, 39, 1791.
9. Kerth, J.; Lobbecke, S. Propellants, Explos., Pyrotech. 2002, 27, 111.
10. Neutz, J.; Grosshardt, O.; Schaufele, S.; Schuppler, H.; Schweikert, W. Propellants, Explos., Pyrotech. 2003, 28, 181.
11. Huynh, M. H. V.; Hiskey, M. A.; Hartline, E. L.; Montoya, D. P.; Gilardi, R. D. Angew. Chem., Int. Ed. 2004, 43, 4924.
12. Churakov, A. M.; Smirnov, O. Y.; Ioffe, S. L.; Strelenko, Y. A.; Tartakovsky, V. A. Eur. J. Org. Chem. 2002, 14, 2342.
13. Huynh, M. H. V.; Hiskey, M. A.; Pollard, C. J.; Montoya, D. P.; Hartline, E. L.; Gilardi, R. D. J. Energy Mater. 2004, 22, 217.
14. Saracoglu, N. Tetrahedron 2007, 63, 4199.
15. Huynh, M. H. V.; Hiskey, M. A.; Chavez, D. E.; Naud, D. L.; Gilardi, R. D. J. Am. Chem. Soc. 2005, 127, 12537.
16. Chavez, D. E.; Hiskey, M. A.; Gilardi, R. D. Org. Lett. 2004, 6, 2889.
17. Huynh, M. H. V.; Hiskey, M. A.; Archuleta, J. G.; Romemer, E. L.; Gilardi, R. Angew. Chem., Int. Ed. 2004, 43, 5658.
18. Hiskey, M. A.; Chavez, D. E.; Naud, D. L. In Sensitive High Nitrogen Compounds. NTIS No: DE-2001-776133, 2001.
19. Chavez, D. E.; Hiskey, M. A. J. Energy Mater. 1999, 17, 357.
20. Talawar, M. B.; Sivabalan, R.; Senthilkumar, N.; Prabhu, G.; Asthana, S. N. J. Hazard. Mater. A 2004, 113, 11.
21. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221.
22. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4907.
23. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
24. Stewart, J. J. P. J. Mol Model. 2004, 10, 155.
25. Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986.
26. Hehre, W. J. Critical Assessment of Molecular Electronic Structure Methods; Wavefunction; Irvine, CA, 1955.
27. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
28. Seminario, J. M.; Politzer, P. Modern Density Functional Theory: A Tool for Chemistry; Elsevier: Amsterdam, 1995.
29. Chen, Z. X.; Xiao, J. M.; Xiao, H. M.; Chiu, Y. N. J. Phys. Chem. A 1999, 103, 8062.
30. Xiao, H. M.; Chen, Z. X. The Modern Theory for Tetrazole Chemistry, 1st ed.; Science Press: Beijing, 2000.
31. Chen, P. C.; Chieh, Y. C.; Tzeng, S. C. J. Mol Struct. (THEOCHEM) 2003, 634, 215.
32. Ju, X. H.; Li, Y. M.; Xiao, H. M. J. Phys. Chem. A 2005, 109, 934.
33. Hahre, W. J.; Radom, L.; Schleyer, P. V. R.; Pole, J. A. Ab Initio Molecular Orbital Theory, 1st ed.; Wiley-Interscience: New York, 1986; p 386.
34. Jursic, B. S. J. Mol Struct. (THEOCHEM) 2000, 499, 137.
35. Wang, F.; Xu, X. J.; Xiao, H. M.; Zhang, J. Acta. Chim. Sin. 2003, 61, 1939.
36. Ju, X. H.; Wang, X.; Bei, F. L. J. Comput. Chem. 2005, 26, 1263.
37. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.
38. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys. 1997, 106, 1063.
39. Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley-Interscience: New York, 1976.
40. Mills, I.; Cvitas, T.; Homann, K.; Kallay, N.; Kuchitsu, K.; Quantities, Units, and Symbols in Physical Chemistry; Blackwell Scientific Publications: Oxford, 1988.
41. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255.
42. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople J. A. Gaussian 98, Revision A.7; Gaussian Inc.: Pittsburgh, PA, 1998.
43. Kamlet, M. J.; Jacobs, S. J. J. Chem. Phys. 1968, 48, 23.
44. Qiu, L.; Xiao, H. M.; Gong, X. D.; Ju, X. H.; Zhu, W. H. J. Hazard. Mater. 2007, 141, 280.
45. David, R. L. Handbook of Chemistry and Physics, 84th ed.; CRC Press: Boca Raton, 2003-2004, Sect 5.
46. Dean, J. A. LANGE'S Handbook of Chemistry, 15th ed.; McGrawHill Book Co.: New York, 1999; Chapter 6.
47. Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. Chemistry Web Book. U.S. Secretary of Commerce on behalf of the U.S.A.; AU rights reserved: National Institute of Standards and Technology, 1998.
48. Chen, Z. X.; Xiao, H. M.; Song, W. Y. J. Mol. Struct (THEOCHEM) 1999, 460, 167.
49. Singh, R. P.; Gao, H. X.; Meshri, D. T.; Shreeve, J. M. Struct. Bonding (Berlin) 2007, 125, 35.
50. Scott, A. P.; Radom, L. J. J. Phys. Chem. 1996, 100, 16502.
51. Owens, F. J. J. Mol. Struct. (THEOCHEM) 1996, 370, 11.
52. Rice, B. M.; Sahu, S.; Owens, F. J. J. Mol. Struct. (THEOCHEM) 1996, 583, 69.
53. Licht, H. H.; Ritter, H. J. Energy Mater. 1994, 12, 223.
54. Talawar, M. B.; Sivabalan, R.; Mukundan, T.; Muthurajan, H.; Sikder, A. K.; Gandhe, B. R.; Subhananda Rao, A. J. Hazard. Mater. 2009, 161, 589.
55. Stine, J. R. J. Energy Mater. 1990, 8, 41.
56. Sing, R. P.; Verma, R. D.; Meshri, D. T.; Shreeve, J. M. Angew. Chem., Int. Ed. 2006, 45, 3584.
57. Zhang, M. X.; Eaton, P. E.; Gilardi, R. D. Angew. Chem. 2000, 112, 422.
58. Zhang, M. X.; Eaton, P. E.; Gilardi, R. D. Angew. Chem., Int. Ed. 2000, 39, 401.