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Open AccessArticle

Structure and Thermal Properties of 2,2′-Azobis(1H-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds

1
Department of High-Energetic Materials, Łukasiewicz Research Network–Institute of Industrial Organic Chemistry, Annopol 6, 03-236 Warsaw, Poland
2
Institute of Physics, University of Silesia, 75 Pułku Piechoty 1, 41-500 Chorzów, Poland
3
Division of High Energetic Materials, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(2), 314; https://doi.org/10.3390/molecules25020314
Received: 12 December 2019 / Revised: 7 January 2020 / Accepted: 9 January 2020 / Published: 13 January 2020
(This article belongs to the Special Issue Advanced Chemistry of Energetic Materials)
A high-nitrogen compound, 2,2′-azobis(1H-imidazole-4,5-dicarbonitrile) (TCAD), was synthesized from commercially available 2-amino-1H-imidazole-4,5-dicarbonitrile. It was characterized with infrared and nuclear magnetic resonance spectroscopy. Its structure was determined by single crystal X-ray diffraction. The crystal of TCAD tetrahydrate is monoclinic, with space group P21/c with crystal parameters of a = 10.2935(2) Å, b = 7.36760(10) Å, c = 20.1447(4) Å, V = 1500.27(5) Å3, Z = 4, and F(000) = 688. Computational methods were used in order to fully optimize the molecular structure, calculate the electrostatic potential of an isolated molecule, and to compute thermodynamic parameters. TCAD has very high thermal stability with temperature of decomposition at 369 °C. Kinetics of thermal decomposition of this compound were studied and apparent energy of activation as well as the maximum safe temperature of technological process were determined. View Full-Text
Keywords: synthesis; high-nitrogen materials; thermal analysis; azo compounds synthesis; high-nitrogen materials; thermal analysis; azo compounds
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Lewczuk, R.; Książek, M.; Gańczyk-Specjalska, K.; Cieślak, K. Structure and Thermal Properties of 2,2′-Azobis(1H-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds. Molecules 2020, 25, 314.

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