Abstract
This paper reports the synthesis, experimental and theoretical studies of a novel inorganic-organic cocrystal energetic material: methylamine triethylenediamine triperchlorate (MT). MT is synthesized by a rapid “one-pot” method. The performance test of MT shows that it is more powerful and has lower sensitivity in comparison to the benchmark energetic material, i.e., 2,4,6-trinitrotoluen (TNT). The molecular and crystal structures of MT are determined by means of x-ray diffraction (XRD). The compound crystallizes in a monoclinic system (space group Pn) with cell dimensions a = 8.975(18), b = 17.836(4), and c = 10.455(2) Å. The band structure and the density of states are calculated by an abbreviated form of the CASTEP code. The first principle tight-binding method within the general gradient approximation is used to study the electronic band structure, density of states, and Fermi energy. The results indicate that the main mechanism of cocrystallization originates from the Cl—O ···H hydrogen bonding between —ClO4 and —NH2.
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References
D. Badgujar, M. Talawar, S. Asthana, and P. Mahulikar, “Advances in Science and Technology of Modern Energetic Materials: an Overview,” J. Hazard. Mater. 151 (2), 289–305 (2008).
B. M. Rice, J. J. Hare, and E. F. C. Byrd, “Accurate Predictions of Crystal Densities Using Quantum Mechanical Molecular Volumes,” J. Phys. Chem. A 111 (42), 10874–10879 (2007).
A. A. Dippold, D. Izsak, and T. M. Klapotke, “A Study of 5-(1,2,4-triazol-c-yl)tetrazol-1-ols: Combining the Benefits of Different Heterocycles for the Design of Energetic Materials,” Chem.-Eur. J. 19 (36), 12042–12051 (2013).
H. Xue, Y. Gao, B. Twamley, and J. M. Shreeve, “Energetic Azolium Azolate Salts,” Inorg. Chem. 44 (14), 5068–5072 (2005).
P. Yin, D. A. Parrish, and J. M. Shreeve, “Energetic Multifunctionalized Nitraminopyrazoles and Their Ionic Derivatives: Ternary Hydrogen-Bond Induced High Energy Density Materials,” J. Amer. Chem. Soc. 137 (14), 4778–4786 (2015).
V. D. Ghule, “Computational Screening of Nitrogen- Rich Energetic Salts Based on Substituted Triazinem” J. Phys. Chem. C 117 (33), 16840–16849 (2013).
J. Zhang and J. M. Shreeve, “3,3—Dinitroamino-4,4— azoxyfurazan and Its Derivatives: An Assembly of Diverse N—O Building Blocks for High-Performance Energetic Materials,” J. Amer. Chem. Soc. 136 (11), 4437–4445 (2014).
A. E. van der Heijden, R. H. Bouma, and A. C. van der Steen, “Physicochemical Parameters of Nitramines Influencing Shock Sensitivity,” Propell., Explos., Pyrotech. 29 (5), 304–313 (2004).
A. K. Sikder and N. Sikder, “A Review of Advanced High Performance, Insensitive and Thermally Stable Energetic Materials Emerging for Military and Space Spplications,” J. Hazard. Mater. 112 (2), 1–15 (2004).
H. Lin, S. G. Zhu, L. Zhang, et al., “Intermolecular Interactions, Thermodynamic Properties, Crystal Structure, and Detonation Performance of HMX/NTO Cocrystal Explosive,” Int. J. Quantum Chem. 113 (10), 1591–1599 (2013).
C. Guo, H. Zhang, X. Wang, et al., “Crystal Structure and Explosive Performance of a New CL-20/Caprolactam Cocrystal,” J. Mol. Struct. 1048 (24), 267–273 (2013).
J. P. Shen, X. H. Duan, Q. P. Luo, et al., “Preparation and Characterization of a Novel Cocrystal Explosive,” Cryst. Growth Des. 11 (5), 1759–1765 (2011).
J. F. Remenar, S. L. Morissette, M. L. Peterson, et al., “Crystal Engineering of Novel Cocrystals of a Triazole Drug with 1,4-Dicarboxylic Acids,” J. Amer. Chem. Soc. 125 (28), 8456–8457 (2003).
D. R. Weyna, T. Shattock, P. Vishweshwar, and M. J. Zaworotko, “Synthesis and Structural Characterization of Cocrystals and Pharmaceutical Cocrystals: Mechanochemistry vs Slow Evaporation from Solution,” Cryst. Growth Des. 9 (2), 1106–1123 (2009).
C. Y. Zhang, Z. W. Yang, X. Q. Zhou, et al., “Evident Hydrogen Bonded Chains Building CL-20-Based Cocrystals,” Cryst. Growth Des. 14 (8), 3923–3928 (2014).
D. Millar, H. Maynard-Casely, D. Allan, et al., “Crystal Engineering of Energetic Materials: Co-Crystals of CL-20,” Crystengcomm. 14 (10), 3742–3749 (2012).
K. B. Landenberger and A. J. Matzger, “Cocrystal Engineering of a Prototype Energetic Material: Supramolecular Chemistry of 2,4,6-trinitrotoluene,” Cryst. Growth Des. 10 (12), 5341–5347 (2010).
O. Bolton and A. J. Matzger, “Improved Stability and Smart-Material Functionality Realized in an Energetic Cocrystal,” Angew. Chem. Int. Edit. 50 (38), 8960–8963 (2011).
K. B. Landenberger and A. J. Matzger, “Cocrystals of 13,5,7-tetranitro-1,3,5,7-tetrazacyclooctane (HMX),” Cryst. Growth Des. 12 (7), 3603–3609 (2012).
O. Bolton, L. R. Simke, P. F. Pagoria, and A. J. Matzger, “High Power Explosive Withgood Sensitivity: A 2:1 Cocrystal of CL-20: HMX,” Cryst. Growth Des. 12 (9), 4311–4314 (2012).
H. Lin, S h.-G. Zhu, and L. Zhang, “Theoretical Investigation of a Novel High Density Cage Compound 4,8,11,14,15-pentanitro-2,6,9,13-tetraoxa-4,8,11,14,15-pentaazaheptacyclo[5.5.1.13,11.15,9] pentadecane,” J. Mol. Model. 19 (3), 1019–1026 (2013).
H. Lin, Sh.-G. Zhu, and H.-Zh. Li, “Synthesis, Characterization, AIM and NBO Analysis of HMX/DMI Cocrystal Explosive,” J. Mol. Struct. 1048 (24), 339–348 (2013).
H. Lin, P.-Y. Chen, and Sh. Zhu, “Computational Study of Pyrazine-Based Derivatives and TheirN-Oxides As High Energy Materials,” J. Phys. Org. Chem. 16 (6), 484–491 (2013).
H. Lin, P.-Y. Chen, Sh.-G. Zhu, et al., “Theoretical Studies on the Thermodynamic Properties, Densities, Detonation Properties, and Pyrolysis Mechanisms of Trinitromethyl-Substituted Aminotetrazole Compounds,” J. Mol. Model. 19 (6), 2413–2422 (2013).
D. Guo, Q. An, S. V. Zybin, et al., “The Co-Crystal of TNT/CL-20 Leads to Decreased Sensitivity Toward Thermal Decomposition from First Principles Based Reactive Molecular Dynamics,” J. Mater. Chem. A. 3 (10), 5409–5419 (2015).
P. Ma, L. Zhang, Sh. Zhu, and H. Chen, “Synthesis, Crystal Structure and DFT Calculation of an Energetic Perchlorate Amine Salt,” J. Cryst. Growth. 335 (1), 70–74 (2011).
P. Ma, L. Zhang, S h.-G. Zhu, and H.-H. Chen, “Synthesis, Structural Investigaqtion, Thermal Destruction, and Properties of a Cocrystal Energetic Perchlorate Amine Salt,” Fiz. Goreniya Vzryva 48 (4), 123–128 (2012) [Combust., Expl., Shock Waves 48 (4), 483–487 (2012)].
G. M. Sheldrick, SHELXL-97. Program for the Refining of Crystal Structure (Univ. of Göttingen, 1997).
M. D. Segall, P. J. D. Lindan, and M. J. Probert, “First-Principles Simulation: Ideas, Illustrations and the CASTEP Code,” J. Phys. 14 (11), 2717–2744 (2002).
T. H. Fischer and J. Almlof, “General Methods for Geometry and Wave Function Optimization,” J. Phys. Chem. 96 (24), 9768–9774 (1992).
M. Anniyappan, S. H. Sonawane, S. J. Pawar, and A. K. Sikder, “Thermal Decomposition and Kinetics of 2,4-dinitroimidazole: An Insensitive High Explosive,” Thermochim. Acta 614, 93–99 (2015).
W. H. Zhu, J. J. Xiao, G. F. Ji, F. Zhao, and H. M.Xiao, “First-Principles Study of the Four Polymorphs of Crystalline Octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine,” J. Phys. Chem. B 111 (44), 12715–12722 (2007).
M. M. Kuklja, E. V. Stefanovich, and A. B. Kunz, “An Excitonic Mechanism of Detonation Initiation in Explosives,” J. Chem. Phys. 112 (7), 3417–3423 (2000).
G. J. Gilman, “Fast, Faster, and Fastest Cracks,” Phil. Mag. Lett. 77 (2), 79–82 (1998).
Q. Wu, W. H. Zhu, and H. M. Xiao, “Pressure-Induced Hydrogen Transfer and Polymerization in Crystalline Furoxan,” RSC Adv. 4 (31), 15995–16004 (2014).
Q. Wu, W. H. Zhu, and H. M. Xiao, “Structural Transformations and Absorption Properties of Crystalline 7-amino-6-nitrobenzodifuroxan under High Pressures,” J. Phys. Chem. C 117 (33), 16830–16839 (2013).
W. Zhu and H. Xiao, “First-Principles Band Gap Criterion for Impact Sensitivity of Energetic Crystals: A Review,” Struct. Chem. 21 (3), 657–665 (2010).
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Original Russian Text © P. Ma, J.-Ch. Jiang, Sh.-G. Zhu.
Published in Fizika Goreniya i Vzryva, Vol. 53, No. 3, pp. 82–92, May–June, 2017.
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Ma, P., Jiang, JC. & Zhu, SG. Synthesis, XRD and DFT studies of a novel cocrystal energetic perchlorate amine salt: Methylamine triethylenediamine triperchlorate. Combust Explos Shock Waves 53, 319–328 (2017). https://doi.org/10.1134/S0010508217030091
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DOI: https://doi.org/10.1134/S0010508217030091