Synthesis and Characterization of Four Energetic Transition Metal Complexes of 3,4-Diamino-1,2,4-triazole

• Autorzy: Yin X. , Jin X. , Xu C.-X. , He P. , Wang K. , Zhang J.-G.
• Języki publikacji: EN

Abstrakty

EN

Four complexes with the formula of [M5(DATr)12~14(H2O)6](ClO4)10 (M = Mn (1), Co (2), Ni (3), Zn (4)) about their synthesis, structures and some energetic properties (such as sensitivities tests) have been described, where the DATr here denotes 3,4-diamino-1,2,4-triazole. These four compounds are all light metallic complexes with good thermal stability. The structures of 2-4 were determined by single-crystal X-ray diffraction, and the crystal structures mainly consist of penta-nuclear units. All the structures have a common interesting property in which DATr plays a role of bi-dentate ligand. Besides, it is observed from the crystal structure of 4 that DATr can be also act as a mono-dentate ligand. Thermodynamic studies of their decomposition properties and kinetic parameters show that the four complexes have high thermal stabilities. Furthermore, tests of their impact and friction sensitivities show that complexes (2) and (3) can be potential candidates as primary explosives to replace toxic lead azide.

Słowa kluczowe

EN

3,4-diamino-1,2,4-triazole; theoretic study; crystal structure; thermal stability; sensitivity

• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2016
• Tom: Vol. 13, no. 2
• Strony: 301--320
• Opis fizyczny: Bibliogr. 23 poz., rys., tab.

Twórcy

autor

Yin X.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, P. R. China

autor

Jin X.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, P. R. China

autor

Xu C.-X.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, P. R. China

autor

He P.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, P. R. China

autor

Wang K.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, P. R. China

autor

Zhang J.-G.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, P. R. China

Bibliografia

• [1] a) Klapötke T.M., Petermayer C., Piercey D.G., Stierstorfer J., 1,3-Bis(nitroimido)-1,2,3-triazolate Anion, the N-Nitroimide Moiety, and the Strategy of Alternating Positive and Negative Charges in the Design of Energetic Materials, J. Am. Chem. Soc., 2012, 134, 20827-20836; b) Kumar A.S., Ghule V.D., Subrahmanyam S., Sahoo A K., Synthesis of Thermally Stable Energetic 1,2,3-Triazole Derivatives, Chem. Eur. J., 2013, 19, 509-518; c) Joas M., Klapötke T.M., Stierstorfer J., Szimhardt N., Synthesis and Characterization of Various Photosensitive Copper(II) Complexes with 5-(1-Methylhydrazinyl)-1H-tetrazole as Ligand and Perchlorate, Nitrate, Dinitramide, and Chloride as Anions, Chem. Eur. J., 2013, 19, 9995-10003.
• [2] a) Tao G.H., Parrish D.A., Shreeve J.M., Nitrogen-rich 5-(1-Methylhydrazinyl) tetrazole and its Copper and Silver Complexes, Inorg. Chem., 2012, 51, 5305-12; b) Tao G.H., Twamley B., Shreeve J.M., Energetic Nitrogen-rich Cu(II) and Cd(II) 5,5’-Azobis(tetrazolate) Complexes, Inorg. Chem., 2009, 48, 9918-9923; c) Zhao H., Qu Z.-R., Ye H.-Y., Xiong R.-G., In situ Hydrothermal Synthesis of Tetrazole Coordination Polymers with Interesting Physical Properties, Chem. Soc. Rev., 2008, 37, 84-100.
• [3] a) Singh R.P., Verma R.D., Meshri D.T., Shreeve J.M., Energetic Nitrogen-Rich Salts and Ionic Liquids. Angew. Chem., Int. Ed., 2006, 45, 3584-3601; b) Fischer N., Joas M., Klapötke T.M., Stierstorfer J., Transition Metal Complexes of 3-Amino-1-nitroguanidine as Laser Ignitible Primary Explosives: Structures and Properties, Inorg. Chem., 2013, 52, 13791-13802; c) Sivabalan R., Anniyappan M., Pawar S.J., Talawar M.B., Gore G.M., Venugopalan S., Gandhe B.R., Synthesis, Characterization and Thermolysis Studies on Triazole and Tetrazole Based High Nitrogen Content High Energy Materials, J. Hazard. Mater., 2006, 137, 672-680; d) Talawar M.B., Sivabalan R., Mukundan T., Muthurajan H., Sikder A.K., Gandhe B.R., Rao A.S., Environmentally Compatible Next Generation Green Energetic Materials (GEMs), J. Hazard. Mater., 2009, 161, 589-607; e) Cui Y., Zhang J., Zhang T., Yang L., Zhang J., Hu X., Synthesis, Structural Investigation, Thermal Decomposition Mechanism and Sensitivity Properties of an Energetic Compound [Cd(DAT)6](ClO4)2 (DAT=1,5-diaminotetrazole), J. Hazard. Mater., 2008, 160, 45-50; f) Zhang J.-G., Li Z.-M., Zang Y., Zhang T.-L., Shu Y.-J., Yang L., Power P.P., Synthesis, Structural Investigation and Thermal Properties of a Novel Manganese Complex Mn2(DAT)2Cl4(H2O)4 (DAT=1,5-diaminotetrazole), J. Hazard. Mater., 2010, 178, 1094-1099; g) Geisberger G., Klapötke T.M., Stierstorfer J., Copper Bis(1-methyl-5-nitriminotetrazolate): A Promising New Primary Explosive, Eur. J. Inorg. Chem., 2007, 4743-4750.
• [4] a) Yang Q., Wei Q., Chen S.-P., Zhang G.-C., Zhou C.-S., Gao S.-L., Solid State Synthesis, Thermodynamics and Catalytic Combustion Effect of a High Energy Nickel(II) Coordination Compound, J. Anal. Appl. Pyrolysis, 2013, 99, 66-70; b) Izsák D., Klapötke T.M., Reuter S., Rösener T., Silver Salt and Derivatives of 5-Azido-1H-1,2,4-triazole-3-carbonitrile, Z. Anorg. Allg. Chem., 2013, 639, 899-905; c) Cudzilo S., Nita M., Synthesis and Explosive Properties of Copper(II) Chlorate(VII) Coordination Polymer with 4-Amino-1,2,4-Triazole Bridging Ligand, J. Hazard. Mater., 2010, 177, 146-9; d) Cudziło S., Trzciński W., Nita M., Michalik S., Krompiec S., Kruszyński R., Kusz J., Preparation, Crystal Structure and Explosive Properties of Copper(II) Perchlorate Complex with 4-Amino-1,2,4-Triazole and Water, Propellants Explos. Pyrotech., 2011, 36, 151-159; e) Wang S.- W., Yang L., Feng J.-L., Wu B.-D., Zhang J.-G., Zhang T.-L., Zhou Z.-N., Synthesis, Crystal Structure, Thermal Decomposition, and Sensitive Properties of Two Novel Energetic Cadmium(II) Complexes Based on 4-Amino-1,2,4-triazole, Z. Anorg. Allg. Chem., 2011, 637, 2215-2222; f) Zhang G.-F., Gao L., Li P., Zhao F.-Q., Fan X.-Z., Chen N., Xiang X.-P., Gao H.-C., Wang J., Structural Diversity in Trinuclear Nickel(II) Complexes of 3,5-Diamino-1,2,4-Triazole, J. Coord. Chem., 2011, 64, 3551-3559.
• [5] a) Li S., Wang Y., Qi C., Zhao X., Zhang J., Zhang S., Pang S., 3D Energetic Metal-Organic Frameworks: Synthesis and Properties of High Energy Materials, Angewandte Chemie Int. Ed., 2013, 52, 1-6; b) Zhang Q., Shreeve J.M., Metal Organic Frameworks as High Explosives: A New Concept for Energetic Materials, Angewandte Chemie Int. Ed., 2014, 53, 2540-2542; c) Zhang S., Liu X., Yang Q., Su Z., Gao W., Wei Q., Xie G., Chen S., Gao S., A New Strategy for Storage and Transportation of Sensitive High-Energy Materials: Guest-Dependent Energy and Sensitivity of 3D Metal-Organic-Framework-Based Energetic Compounds, Chem. Eur. J., 2014, 20, 7906-7910.
• [6] Gou Y.-T., Yue F., Chen H.-M., Liu G., Sun D.-C., Syntheses and Structures of 3d–4d Heterometallic Coordination polymers Based on 4-Amino-1,2,4-Triazole, J. Coord. Chem., 2013, 66, 1889-1896.
• [7] Xu C.-X., Yin X., Jin X., He P., Qin J., Zhang J.-G., Jiao J.-S., Two Coordination Polymers with 3-Hydrazino-4-amino-1,2,4-triazole as Ligand: Synthesis, Crystal Structures, and Non-Isothermal Kinetic Analysis, J. Coord. Chem., 2014, 67, 2004- 2015.
• [8] Yang Q., Xie G., Chen S., Gao S., Synthesis, Structure and Thermodynamics of Supermolecular Compound [Ni3(Hdatrz)6(sca)2(H2O)4]sca·11H2O (Hdatrz = 3,5-diamino-1,2,4-triazole, H2sca = succinic acid), J. Therm. Anal. Calorim., 2011, 110, 979-984.
• [9] a) Konovalova I.S., Shishkina S.V., Paponov B.V., Shishkin O.V., Analysis of the Crystal Structure of Two Polymorphic Modifications of 3,4-Diamino-1,2,4-Triazole Based on the Energy of the Intermolecular Interactions, Cryst. Eng. Comm., 2010, 12, 909-916; b) Konovalova I.S., Nelyubina Y.V., Lyssenko K.A., Paponov B.V., Shishkin O.V., Intra- and Intermolecular Interactions in the Crystals of 3,4-Diamino-1,2,4-triazole and Its 5-Methyl Derivative. Experimental and Theoretical Investigations of Charge Density Distribution, J. Phys. Chem. A, 2011, 115, 8550-8562; c) Naik A.D., Tinant B., Léonard A., Marchand-Brynaert J., Su B.-L., Garci Y., (Di)aminoguanidine Functionalization through Transamination: an Avenue to an Auspicious Class of Supramolecular Synthons, Cryst. Growth Des., 2011, 11, 4034-4043.
• [10] Jin X., Zhang J.-G., Xu C.-X., Yin X., He P., Qin Q., Eco-friendly Energetic Complexes Based on Transition Metal Nitrates and 3,4-Diamino-1,2,4-triazole (DATr), J. Coord. Chem., 2014, 67, 3202-3215.
• [11] Wu J.-T., Zhang J.-G., Yin X., Sun M., Zhang T.-L., Synthesis, Characterization, and Thermal Analysis of Two Energetic Ionic Salts Based on 3,4-Diamino-1,2,4-triazole (DATr), Z. Anorg. Allg. Chem., 2013, 639, 2354-2358.
• [12] Sheldrick G.M. SHELXS-97, University of Göttingen: Germany: 1990.
• [13] Sheldrick G.M. SHELXL-97, University of Göttingen: Germany: 1997.
• [14] Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Jr., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Iiskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., Pople J.A., GAUSSIAN 9 (Revision A.01): Gaussian, Inc, 2009.
• [15] Lu T. Multiwfn. http://multiwfn.codeplex.com/.
• [16] Alghool S., Slebodnick C., One Dimensional Structure of Zn(II) Metal Organic Framework (MOF) Assembled Rapidly at Room Temperature: Structural, Thermal Study, and Luminescent Properties, J. Inorg. Organomet. Polym. Mater., 2014, 24, 644-651.
• [17] a) Tao G.-H., Huang Y., Boatz J.A., Shreeve J.M., Energetic Ionic Liquids based on Lanthanide Nitrate Complex Anions, Chem. Eur. J., 2008, 14, 11167-11173;b) Steinhauser G., Klapötke T.M., “Green” Pyrotechnics: A Chemists’ Challenge, Angew. Chem., Int. Ed., 2008, 47, 3330-3347.
• [18] Kissinger H.E., Anal. Chem., 1957, 29, 1702-1706.
• [19] Ozawa T., Bull. Chem. Soc. Jpn., 1965, 38, 1881-1886.
• [20] a) Suceska M., Test Methods for Explosives, Springer, New York, 1995; p. 21 (impact), p. 27 (friction); b) Walley S.M., Field J.E., Biers R.A., Proud W.G., Williamson D.M. Jardine A.P., Propell. Explos. Pyrotech. 2015, 40, 351-365.
• [21] Karaghiosoff K., Klapötke T.M., Miró Sabaté C., Energetic Silver Salts with 5-Aminotetrazole Ligands, Chem. Eur. J., 2009, 15, 1164-1176.
• [22] Fischer D., Klapötke T.M., Piercey D.G., Stierstorfer J., Copper Salts of Halo Tetrazoles: Laser-Ignitable Primary Explosives, J. Energ. Mater., 2012, 30, 40-54.
• [23] Impact: insensitive >40 J, less sensitive ≥35 J, sensitive ≥4 J, very sensitive ≤3 J; Friction: insensitive > 360 N, less sensitive = 360 N, sensitive < 360 N and > 80 N, very sensitive ≤ 80 N, extremely sensitive ≤ 10 N, According to: Recommendations on the Transport of Dangerous Goods, Manual of Tests and Criteria, 4th ed., United Nations, New York, 1999.

Uwagi

Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę.