The structure and decomposition chemistry of isomer defects in a crystalline DADNE

Journal of Energetic Materials

Volumn 28, Issue SUPPL. 1, 2010, Pages 128-139

  Kimmel, Anna V ^a   Sushko, Peter V ^a   Kuklja, Maija M ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF MARYLAND   (United States)

Author keywords

DADNE; Defects; Energetic materials; Explosive decomposition; Isomerization; Organic molecular crystals; Thermal chemistry

Indexed keywords

EID: 77958601370     PISSN: 07370652     EISSN: 15458822     Source Type: Journal    
DOI: 10.1080/07370651003639389     Document Type: Article

References (21)

1. Latypov, N. V., J. Bergman, A. Langlet, U. Wellmar, and U. Bemm. 1998. Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene. Tetrahedron, 54: 11525.
2. Östmark, H., A. Langlet, H. Bergman, N. Wingborg, U. Wellmar, and U. Bemm. 2000. FOX-7-A New Explosive with Low Sensitivity and High Performance. In Proceedings of the 11th International Detonation Symposium. Arlington, VA: ONR.
3. Politzer, P., M. C. Concha, M. E. Grice, M. E. Murray, P. Lane, and D. Habibollazadeh. 1998. Computational investigation of the structures and relative stabilities of amino=nitro derivatives of ethylene. Journal of Molecular Structure (Theochem), 75: 425.
4. Hervé, G., G. Jacob, and N. Latypov. 2005. The reactivity of 1,1-diamino-2,2-dinitroethene (FOX-7). Tetrahedron, 61: 6743-6745.
5. Bellamy, A. J., N. V. Latypov, and P. Goede. 2002. Transamination reactions of 1,1-diamino-2,2-dinitroethene (FOX-7). Journal of Chemical Research, 641-644.
6. Bellamy, A. J. 2007. FOX-7 (1,1-Diamino-2,2-dinitroethene). Structure and Bonding, 125: 1-33.
7. From a chemical standpoint, the structure of 1,1-diamino-2,2-dinitroethelene excludes the formation of geometric and rotational isomers. The presence of the latter may be assumed only under high temperature, which would weaken the C1/4C bond and induce rotations of functional groups around this bond. The structure of 1,2-diamino-1,2-dinitroethylene would theoretically allow for two geometric isomers, trans-and cis-, to exist.
8. Becke, A. D. 1993. A new mixing of Hartree-Fock and local density-functional theories. Journal of Chemical Physics, 98: 5548.
9. Lee, C., W. Yang, and R. G. Parr. 1998. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37: 785.
10. Frisch, M. J., G. W. Trucks, H. B. Schlegel, et al. 2003. GAUSSIAN 03. Wallingford, CT: Gaussian Inc.
11. Sushko, P., A. L. Shluger, and C. R. A. Catlow. 2000. Relative energies of surface and defect states: Ab initio calculations of the MgO (001) surface. Surface Science, 450: 153.
12. 3. Journal of the American Chemical Society, 129: 942.
13. Kimmel, A. V., P. V. Sushko, A. L. Shluger, and M. M. Kuklja. 2009. Modeling proton transfer and polarons in a molecular crystal diamino-dinitroethylene. Physical Review B, 80: 134108.
14. Kimmel, A. V., P. V. Sushko, A. L. Shluger, and M. M. Kuklja. 2008. Effect of molecular and lattice structure on hydrogen transfer in molecular crystals of diamino-dinitroethylene and triamino-trinitrobenzene. Journal of Physical Chemistry A, 112: 4496.
15. Perdew, J. P., K. Burke, and M. Ernzerhof. 1996. Generalized gradient approximation made simple. Physical Review Letters, 77: 3865.
16. Mills, G., H. Jonsson, and G. K. Schenter. 1995. Reversible work transition state theory: Application to dissociative adsorption of hydrogen. Surface Science, 324: 305.
17. Kresse, G. and J. Hafner. 1993. Ab initio molecular dynamics for open-shell transition metals. Physical Review B, 48: 13115.
18. Note that DADNE exists in three different polymorphs (alpha, beta, and gamma) with different torsion angles; see, for example, Evers, J., T. M. Klapötke, P. Mayer, G. Oehlinger, and J. Welch, J. 2006. α-and β-FOX-7, Polymorphs of a high energy density material, studied by X-ray single crystal and powder investigations in the temperature range from 200 to 423K. Inorganic Chemistry, 45: 4996;
19. Crawford, M.-J., J. Evers, M. Göbel, T. M. Klapötke, P. Mayer, G. Oehlinger, and J. M. Welch. 2007. γ-FOX-7: Structure of a high energy density material immediately prior to decomposition. Propellants, Explosives, Pyrotechnics, 32: 478.
20. Kuklja, M. M. and S. N. Rashkeev. 2007. Shear-strain-induced chemical reactivity of layered molecular crystals. Applied Physics Letters, 90: 151913.
21. Kuklja, M. M. and S. N. Rashkeev. 2010. Accelerated mechanochemistry in nitroarenes. Journal of Physical Chemistry Letters, 1: 363.