Interaction of 1,1-Diamino-2,2-Dinitroethylene with Aluminum and Gallium Admixture - DFT Treatment

  • Lemi Türker Department of Chemistry, Middle East Technical University, Üniversiteler, Eskişehir Yolu No: 1, 06800 Çankaya/Ankara, Turkey
Keywords: 1,1-diamino-2,2-dinitroethylene, FOX-7, DADNE, aluminum, gallium, DFT

Abstract

Interaction of 1,1-diamino-2,2-dinitroethylene with nAl+mGa (n,m:1,2) admixture has been investigated within the constraints of density functional theory at the level of UB3LYP/6-311++G(d,p). Various multiplicity states arise for the composites due to the open-shell ground state electronic configurations of Al and Ga atoms. The composites are electronically stable, thermodynamically exothermic and have favorable Gibbs’ free energy of formation values. Various quantum chemical properties have been obtained and discussed. The calculated UV-VIS spectra indicate that some of the composites are infrared absorbing systems beyond 700 nm.

References

J.P. Agrawal, High Energy Materials, Weinheim: Wiley-VCH, 2010. https://doi.org/10.1002/9783527628803

P. Politzer and J.S. Murray, Energetic Materials, Part 1, Amsterdam: Elsevier, 2003.

I.J. Lochert, FOX-7 - A new insensitive explosive FOX-7, DSTO Aeronautical and Maritime Research Laboratory 506 Lorimer St, Fishermans Bend, Victoria 3207 Australia 2001, AR-012-065, November 2001.

N. V. Latypov, J. Bergman, A. Langlet, U. Wellmar and U. Bemm, Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene, Tetrahedron 54 (1998), 11525-11536. https://doi.org/10.1016/S0040-4020(98)00673-5

U. Bemm and H. Östmark, 1,1-diamino-2,2-dinitroethylene: a novel energetic material with infinite layers in two dimensions, Acta Cryst. C54 (1998), 1997-1999. https://doi.org/10.1107/S0108270198007987

N.V. Latypov, A. Langlet and U. Wellmar, New chemical compound suitable for use as an explosive, intermediate and method for preparing the compound, World Patent WO99/03818, 1999.

H. Östmark, H. Bergman, U. Bemm, P. Goede, E. Holmgren, M. Johansson, A. Langlet, N.V. Latypov, A. Pettersson, M.L. Pettersson, N. Wingborg, C. Vörde, H. Stenmark, L. Karlsson and M. Hihkiö, 2,2-Dinitroethene-1,1-diamine (FOX-7) - properties, analysis and scale-up, 32nd International Annual Conference of ICT on Energetic Materials- Ignition, Combustion and Detonation, Karlsruhe, Germany, 2001.

H. Östmark, A. Langlet, H. Bergman, N. Wingborg, U. Wellmar and U. Bemm, FOX-7 – a new explosive with low sensitivity and high performance, The 11th International Detonation Symposium, Colorado, USA, 1998.

H. Bergman, H. Ostmark, A. Pettersson, M.L. Petterson, U. Bemm and M. Hihkio, Some initial properties and thermal stability of FOX-7, Insensitive Munitions and Energetic Materials Symposium (NDIA), Tampa, Florida, USA, 1999.

W. A. Trzciński and A. Belaada, 1,1-Diamino-2,2-dinitroethene (DADNE, FOX-7) – Properties and formulations (a review), Central European Journal of Energetic Materials 13(2) (2016), 527-544. https://doi.org/10.22211/cejem/65000

B. Janzon, H. Bergman, C. Eldsater, C. Lamnevik and H. Ostmark, FOX-7 – A novel, high performance, low vulnerability high explosive for warhead applications, 20th Int. Symp. Ballistics, Orlando, Florida, USA, September 23-27, 2002.

Y.N. Matyushin, G.T. Afanas’ev, V.P. Lebedev, M.N. Mahov and V.I. Pepekin, TATB and FOX-7: Thermochemistry, performance, detonability, sensitivity, 34th Int. Annu. Conf. ICT, Karlsruhe, Germany, June 24-27, 2003.

A.J. Bellamy, N.V. Latypov and P. Goede, Studies on the nitration of new potential precursors for FOX-7, New Trends Res. Energ. Mater. Proc. Semin. 7th, Pardubice, Czech Republic, April 20-22, 2004.

S. Cudziło, Z. Chyłek and R. Diduszko, Crystallization and characterization of 1,1- diamino-2,2-dinitroethene (DADNE), 36th Int. Annu. Conf. ICT, Karlsruhe, Germany, June 28-July 1, 2005.

W.A. Trzciński, S. Cudziło, Z. Chyłek and L. Szymańczyk, Investigation of sensitivity and detonation properties of FOX-7, 37th Int. Annu. Conf. ICT, Karlsruhe, Germany, June 27-30, 2006.

M. Anniyappan, M.B. Talawar, G.M. Gore, S. Venugopalan and B.R. Gandhe, Synthesis, characterization and thermolysis of 1,1-diamino-2,2-dinitroethylene (FOX-7) and its salts, J. Hazard. Mater. B 137 (2006), 812-819. https://doi.org/10.1016/j.jhazmat.2006.03.034

W. A. Trzciński, S. Cudziło, Z. Chyłek and L. Szymańczyk, Detonation properties of 1,1-diamino-2,2-dinitroethene (DADNE), J. Hazard. Mater. 157 (2008), 605-612. https://doi.org/10.1016/j.jhazmat.2008.01.026

V.S. Mishra, S.R. Vadali, R.K. Garg, V.S. Joshi, R.D. Wasnik and S. Asthana, Studies on FOX-7 based melt cast high explosive formulations, Cent. Eur. J. Energ. Mater. 10(4) (2013), 569-580.

N.V. Latypov, M. Johansson, E. Holmgren, E.V. Sizova, V.V. Sizov and A.J. Bellamy, On the synthesis of 1,1-diamino-2,2-dinitroethene (FOX-7) by nitration of 4,6- dihydroxy-2-methylpyrimidine, Org. Process Res. Dev. 11 (1) (2007), 56-59. https://doi.org/10.1021/op068010t

Y. Zhang, Q. Sun, K. Xu, J. Song and F. Zhao, Review on the reactivity of 1,1-diamino- 2,2-dinitroethylene (FOX-7), Propellants Explos. Pyrotech. 41 (2016), 35-52. https://doi.org/10.1002/prep.201500065

K. Baum, N.V. Nguyen, R. Gilardi, J.L. Flippen-Anderson and C. George, Nitration of 1,1-diamino-2,2-dinitroethylenes, J. Org. Chem. 57 (1992), 3026-3030. https://doi.org/10.1021/jo00037a015

T.M. Klapötke, Chemistry of High-Energy Materials, Berlin: De Gruyter, 2011.

J. Evers, T. M. Klapötke, P. Mayer, G. Oehlinger and J. Welch, 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 423 K, Inorg. Chem. 45 (2006), 4996-5007. https://doi.org/10.1021/ic052150m

M.J. Crawford, J. Evers, M. Göbel, T.M. Klapötke, P. Mayer, G. Oehlinger and J.M. Welch, γ-FOX-7: Structure of a high energy density material immediately prior to decomposition, Propellants Explos. Pyrotech. 32 (2007), 478-495. https://doi.org/10.1002/prep.200700240.

A. Gindulytė, L. Massa, L. Huang and J. Karle, Proposed mechanism of 1,1-diamino- dinitroethylene decomposition: a density functional theory study, J. Phys. Chem. A 103 (1999), 11045-11051. https://doi.org/10.1021/jp991794a

Z.A. Dreger, A.I. Stash, Z.G. Yu, Y.S. Chen, Y. Tao and Y.M. Gupta, High-pressure crystal structures of an insensitive energetic crystal: 1,1-diamino-2,2-dinitroethene, J. Phys. Chem. C 120 (2) (2016), 1218-1224. https://doi.org/10.1021/acs.jpcc.5b10644

H. Lips and K. Menke, FOX-7/GAP rocket propellants for a shoulder launched projectile, 27th International Symposium on Ballistics, Freiburg, Germany: April 22-26, 2013.

T. Zhou, Y. Li, K. Xu, J. Song and F. Zhao, The new role of 1,1-diamino-2,2-dinitroethylene (FOX-7): two unexpected reactions, New J. Chem. 41 (2017), 168-176. https://doi.org/10.1039/c6nj03370a

H. Gao and J.M. Shreeve, Recent progress in taming FOX-7 (1,1-diamino-2,2- dinitroethene), RSC Adv. 6 (2016), 56271-56277. https://doi.org/10.1039/c6ra12412g

J. Zhao, X.-J. Feng, H.-T. Xu, X. Tian and B. Feng, Shock initiation characteristics of FOX-7 and RDX based aluminized explosive, Huozhayao Xuebao/Chinese Journal of Explosives and Propellants 39(4) (2016), 42-45 and 50.

D.B. Lempert, E.M. Dorofeenko and Y. Shu, Energy potential of solid composite propellants based on 1,1-diamino-2,2-dinitroethylene, Russian Journal of Physical Chemistry B 10(3) (2016), 483-489. https://doi.org/10.1134/S1990793116030258

C.-C. Ye, F.-Q. Zhao, S.-Y. Xu and X.-H. Ju, Density functional theory studies on adsorption and decomposition mechanism of FOX-7 on Al13 clusters, Canadian Journal of Chemistry 91(12) (2013), 1207-1212. https://doi.org/10.1139/cjc-2013-0334

L. Bian, Y. Shu, J. Xu and L. Wang, Computational investigation on the new high energy density material of aluminum enriched 1,1-diamino-2,2-dinitroethylene, Journal of Molecular Modeling 19(1) (2013), 131-138. https://doi.org/10.1007/s00894-012-1533-x

C. Ye, X. Ju, F. Zhao and S. Xu, Adsorption and decomposition mechanism of 1,1-diamino-2,2-dinitroethylene on Al(111) surface by periodic DFT calculations, Chin. J. Chem. 30(10) (2012), 2539-2548. https://doi.org/10.1002/cjoc.201200470

D.C. Sorescu, J.A. Boatz and D.L. Thompson, First-principles calculations of the adsorption of nitromethane and 1,1-diamino-2,2-dinitroethylene (FOX-7) molecules on the Al(111) surface, J. Phys. Chem. B 107(34) (2003), 8953-8964. https://doi.org/10.1021/jp030258m

J. Taylor, Solid Propellent and Exothermic Compositions, London: George Newnes Ltd., 1959.

J.J.P Stewart, Optimization of parameters for semiempirical methods I. Method, J. Comput. Chem. 10 (1989), 209-220. https://doi.org/10.1002/jcc.540100208

J.J.P Stewart, Optimization of parameters for semi empirical methods II. Application, J. Comput. Chem. 10 (1989), 221-264. https://doi.org/10.1002/jcc.540100209

A. R. Leach, Molecular Modeling, Essex: Longman, 1997.

P. Fletcher, Practical Methods of Optimization, New York: Wiley, 1990.

W. Kohn and L. Sham, Self-consistent equations including exchange and correlation effects, Phys. Rev. 140 (1965), A1133-A1138. https://doi.org/10.1103/PhysRev.140.A1133

R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, London: Oxford University Press, 1989.

C.J. Cramer, Essentials of Computational Chemistry, Chichester, West Sussex: Wiley, 2004.

A.D. Becke, Density-functional exchange-energy approximation with correct asymptotic behavior, Phys. Rev. A 38 (1988), 3098-3100. https://doi.org/10.1103/PhysRevA.38.3098

S.H. Vosko, L. Wilk and M. Nusair, Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Can. J. Phys. 58 (1980), 1200-1211. https://doi.org/10.1139/p80-159

C. Lee, W. Yang and R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B 37 (1988), 785-789. https://doi.org/10.1103/PhysRevB.37.785

SPARTAN 06, Wavefunction Inc., Irvine CA, USA, 2006.

P.J. Durant and B. Durant, Introduction to Advanced Inorganic Chemistry, London: Longman, 1972.

J.G. Stark and H.G. Wallace, Chemistry Data Book, 2nd ed., London: John Murray Pub., 1982.

L. Türker, Interaction of 1,1-diamino-2,2-dinitroethylene and gallium - DFT treatment, Earthline Journal of Chemical Sciences 2(2) (2019), 271-291. https://doi.org/10.34198/ejcs.2219.271291

V. Anbu, K.A. Vijayalakshmi, R. Karunathan, A.D. Stephen and P.V. Nidhin, Explosives properties of high energetic trinitrophenyl nitramide molecules: A DFT and AIM analysis, Arabian Journal of Chemistry 12(5) (2019), 621-632. https://doi.org/10.1016/j.arabjc.2016.09.023

N.R. Badders, C. Wei, A.A. Aldeeb, W.J. Rogers and M.S. Mannan, Predicting the impact sensitivities of polynitro compounds using quantum chemical descriptors, Journal of Energetic Materials 24 (2006), 17-33. https://doi.org/10.1080/07370650500374326

Published
2020-11-22
How to Cite
Türker, L. (2020). Interaction of 1,1-Diamino-2,2-Dinitroethylene with Aluminum and Gallium Admixture - DFT Treatment. Earthline Journal of Chemical Sciences, 5(1), 87-103. https://doi.org/10.34198/ejcs.5121.87103
Section
Articles