Some DADNE Originated Cyclic Isomers - A DFT Study
Abstract
Diaminodinitroethylene (DADNE) has three constitutional isomers, geminal, cis and trans. The geminal one is the well known FOX-7 explosive. It is a push-pull type molecule. In the present study, within the restrictions of density functional theory at the level of B3LYP/6-311++G(d,p), two cyclic dimeric structures of DADNE are investigated quantum chemically. Also their mono ionic forms have been investigated (unrestricted treatment). All the structures are found to be stable. Various quantum chemical and spectral data are collected computationally and discussed.
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, DSTO Aeronautical and Maritime Research Laboratory, 506 Lorimer St, Fishermans Bend, Victoria 3207 Australia, 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 Crystallogr. C 54 (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, Patent WO99/03818, 1999.
H. Östmark, H. Bergman, U. Bemm, P. Goede, E. Holmgren, M. Johansson, A. Langlet, N. V. Latypov, A. Petterson, M. L. Petterson, N. Wingborg, C. Vörde, H. Stenmark, L. Karlsson and M. Hihkiö, 2,2-dinitro-ethene-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), Cent. Eur. J. Energ. Mater. 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 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. Ganghe, 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. (CEJEM) 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
T. M. Klapötke, Chemistry of High-Energy Materials, Berlin: De Gruyter, 2011. https://doi.org/10.1515/9783110227840
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
J. Evers, T. M. Klapötke, F. Mayer, G. Oehlinger, J. Welch, α- and γ-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. 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.
S. Karlsson, H. Östmark, C. Eldsäter, T. Carlsson, H. Bergman, S. Wallin and A. Pettersson, Detonation and sensitivity properties of FOX-7 and formulations containing FOX-7, FOI, Swedish Defence Research Agency, Grindsjöns Research Center, SE-147 25, Tumba, Sweden, 2002.
L. Türker and S. Varış, Effects of epoxidation and nitration on ballistic properties of FOX-7, Z. Anorg. Allg. Chem. (ZAAC) 639 (2013), 982-987. https://doi.org/10.1002/zaac.201300086
H. Dorsett, Computational Studies of FOX-7, A New Insensitive Explosive, DSTO Aeronautical and Maritime Research Laboratory, PO Box 1500, Salisbury, South Australia, AR-011-596, September, 2000.
X. Fang and W. G. McLuckie, Laser ignitibility of insensitive secondary explosive 1,1-diamino-2,2-dinitroethene (FOX-7), J. Hazard. Mater. 285(21) (2015), 375-82. https://doi.org/10.1016/j.jhazmat.2014.12.006
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. (2017), 1. 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. (2016), 1. https://doi.org/10.1039/C6RA12412G
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, J. Phys. Rev. 140 (1965), 1133-1138. 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.
M. J. S. Dewar, The Molecular Orbital Theory of Organic Chemistry, New York: McGraw-Hill, 1969.
M. J. S. Dewar and R. C. Dougherty, The PMO Theory of Organic Chemistry, New York: Plenum-Rosetta, 1975. https://doi.org/10.1007/978-1-4613-4404-9
I. S. Dmitriev, Molecules Without Chemical Bonds, Moscow: Mir Pub., 1981.
L. Türker, Recent developments in the theory of explosive materials (371-404), in: Jansen JT (Ed.), Explosive Materials, New York: NOVA, 2011.
I. Fleming, Frontier Orbitals and Organic Chemical Reactions, NY: Wiley, 1976.
V. Anbu, K. A. Vijayalakshmi, R. Karunathan, A. David 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
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