Theoretical prediction of 2,4,6-trinitro-1,3,5-triazine (TNTA). A new, powerful, high-energy density material?

Journal of the American Chemical Society

Volumn 118, Issue 48, 1996, Pages 12244-12245

  Korkin, Anatoli A ^a   Bartlett, Rodney J ^a  

^a UNIVERSITY OF FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,4,6 TRINITRO 1,3,5 TRIAZINE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; THERMODYNAMICS;

EID: 0030443057     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962744b     Document Type: Article

References (29)

1. Korkin, A. A.; Leszczynski, J.; Bartlett, R. J. J. Phys. Chem. In press.
2. (a) Beyer, W. Handbook of Organic Chemistry; Prentice Hall: London, 1996.
3. (b) Smolin, E. M.; Rapoport, L. s-Triazines and Derivatives; Interscience: New York, 1959.
4. (c) Porter, A. E. A. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 4, p 145.
5. Finger, H. J. Prakt. Chem. 2 1907, 75, 103.
6. (a) Magers, D. H.; Salter, E. A.; Bartlett, R. J.; Salter, C.; Hess, B. A., Jr.; Schaad, L. J. J. Am. Chem. Soc. 1988, 110, 3435.
7. (b) Lauderdale, W. J.; Myers, W. J.; Bernholdt, D. E.; Stanton, J. F.; Bartlett, R. J. Proceedings of the High Energy Density Materials Contractors Conference; 25-28 February, Long Beach, CA; Phillips Laboratory: Edwards Air Force Base, CA, 1990; p 121.
8. (c) Lauderdale, W. J.; Stanton, J. F.; Bartlett, R. J. J. Phys. Chem. 1992, 96, 1174.
9. (d) Ferris, K. F.; Bartlett, R. J. J. Am. Chem. Soc. 1992, 114, 8302.
10. (e) Stanton, J. F.; Gauss, J.; Bartlett, R. J.; Helgaker, T.; Jorgensen, P.; Jensen, H. J.; Taylor, P. R. J. Chem. Phys. 1992, 97, 1211.
11. (f) Cernusak, I.; Beck, S.; Bartlett, R. J. J. Phys. Chem. 1992, 96, 10284.
12. (g) Cernusak, I.; Urban, M.; Ertl, P.; Bartlett, R. J. J. Am. Chem. Soc. 1992, 114. 10955.
13. (h) Korkin, A. A.; Schleyer, P. v. R.; Boyd, R. J. Chem. Phys. Lett. 1994, 227, 312.
14. (i) Korkin, A. A.; Balkova, A.; Bartlett, R. J.; Boyd, R. J.; Schleyer, P. v. R. J. Phys. Chem. 1996, 100, 5702.
15. ACES II is a program product of the Quantum Theory Project, University of Florida, Gainesville, FL, 1996; Stanton, J. F.; Gauss, J.; Watts, J. D.; Nooijen, M.; Oliphant, N.; Perera, S. A.; Szalay, P. G.; Lauderdale, W. J.; Gwaltney, S. R.; Beck, S.; Balkova, A.; Bernholdt, D. E.; Baeck, K.-K.; Rozyczko, P.; Sekino, H.; Huber, C.; Bartlett, R. J. Integral packages included are VMOL (Almlöf, J.; Taylor, P. R.); VPROPS (Taylor, P. R.); ABACUS (Helgaker, H. J.; Jensen, Aa; Jorgensen, P.; Taylor, P. R.).
16. Harmonic vibrational frequencies of TNTA and reference molecules can be obtained from the authors (korkin@qtp.ufl.edu).
17. Zero-point energies (ZPE) were scaled by 0.9 at HF/6-31G*and by 0.95 at MBPT(2)/6-31G*as recommended: Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory. Wiley: New York, 1986.
18. CN = 1.339 Å and ∠CNC = 114.0° at MBPT(2)/6-31G**: Creuzet, S.; Langlet, J. Chem. Phys. Lett. 1993, 208, 511.
19. Pyckhout, W.; Callaerts, I.; Van Anselnoy, C.; Rae, A. I. M.; Pawley, G. S. J. Mol. Struct. 1986, 147, 321.
20. At MBPT(2)/6-31G*, the CN bond lengths are 1.470 Å and 1.459 Å in planar minimum and in 90° rotated transition structures of nitrobenzene, respectively: Slyaposnikov, V. A.; Khaikin, L. S.; Grikina, O. E.; Bock, C. W.; Vilkov, L. V. J. Mol. Struct. 1994, 326, 1.
21. Neutron difraction study of TNB reveals two different molecules in an assymetric unit. Average structural parameters are CC = 1.379 A, CN = 1.477 Å, NO = 1.207 Å, ∠CC(N)C = 123.4°, ∠ONO = 125.1°: Sun Choi, C.; Abel, J. E. Acta Crystallogr. 1972, B28, 193.
22. Benson, S. W. Thermochemical Kinetics. Wiley: New York, 1976.
23. Byström, K. J. Chem. Thermodyn. 1982, 14, 865.
24. Meyer, R. Explosives, 3rd ed.; VCH: Weinheim, 1987; p 71.
25. D. Lempert, private communication.
26. S. Rodgers, private communication.
27. Immirzi, A.; Perini, B. Acta Crystallogr. 1977, A33, 216.
28. K. Christe, private communication.
29. Estimated from the heats of formation of HCN (32.3 kcal/mol in ref 12) and s-triazine (53.9 kcal/mol in ref 13).