Structure and Thermal Properties of 2,2′-Azobis(1<i>H</i>-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds
A high-nitrogen compound, 2,2′-azobis(1<i>H</i>-imidazole-4,5-dicarbonitrile) (TCAD), was synthesized from commercially available 2-amino-1<i>H</i>-imidazole-4,5-dicarbonitrile. It was characterized with infrared and nuclear magnetic resonance spectroscopy. Its stru...
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MDPI AG
2020-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/2/314 |
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| author | Rafał Lewczuk Maria Książek Katarzyna Gańczyk-Specjalska Katarzyna Cieślak |
| author_facet | Rafał Lewczuk Maria Książek Katarzyna Gańczyk-Specjalska Katarzyna Cieślak |
| author_sort | Rafał Lewczuk |
| collection | DOAJ |
| description | A high-nitrogen compound, 2,2′-azobis(1<i>H</i>-imidazole-4,5-dicarbonitrile) (TCAD), was synthesized from commercially available 2-amino-1<i>H</i>-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 P2<sub>1</sub>/c with crystal parameters of a = 10.2935(2) Å, b = 7.36760(10) Å, c = 20.1447(4) Å, V = 1500.27(5) Å<sup>3</sup>, 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. |
| first_indexed | 2024-12-10T10:48:57Z |
| format | Article |
| id | doaj.art-3bdfa64c5ba047ea8d468d57c3b4b174 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T10:48:57Z |
| publishDate | 2020-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3bdfa64c5ba047ea8d468d57c3b4b1742022-12-22T01:52:05ZengMDPI AGMolecules1420-30492020-01-0125231410.3390/molecules25020314molecules25020314Structure and Thermal Properties of 2,2′-Azobis(1<i>H</i>-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic CompoundsRafał Lewczuk0Maria Książek1Katarzyna Gańczyk-Specjalska2Katarzyna Cieślak3Department of High-Energetic Materials, Łukasiewicz Research Network–Institute of Industrial Organic Chemistry, Annopol 6, 03-236 Warsaw, PolandInstitute of Physics, University of Silesia, 75 Pułku Piechoty 1, 41-500 Chorzów, PolandDepartment of High-Energetic Materials, Łukasiewicz Research Network–Institute of Industrial Organic Chemistry, Annopol 6, 03-236 Warsaw, PolandDivision of High Energetic Materials, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, PolandA high-nitrogen compound, 2,2′-azobis(1<i>H</i>-imidazole-4,5-dicarbonitrile) (TCAD), was synthesized from commercially available 2-amino-1<i>H</i>-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 P2<sub>1</sub>/c with crystal parameters of a = 10.2935(2) Å, b = 7.36760(10) Å, c = 20.1447(4) Å, V = 1500.27(5) Å<sup>3</sup>, 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.https://www.mdpi.com/1420-3049/25/2/314synthesishigh-nitrogen materialsthermal analysisazo compounds |
| spellingShingle | Rafał Lewczuk Maria Książek Katarzyna Gańczyk-Specjalska Katarzyna Cieślak Structure and Thermal Properties of 2,2′-Azobis(1<i>H</i>-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds Molecules synthesis high-nitrogen materials thermal analysis azo compounds |
| title | Structure and Thermal Properties of 2,2′-Azobis(1<i>H</i>-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds |
| title_full | Structure and Thermal Properties of 2,2′-Azobis(1<i>H</i>-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds |
| title_fullStr | Structure and Thermal Properties of 2,2′-Azobis(1<i>H</i>-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds |
| title_full_unstemmed | Structure and Thermal Properties of 2,2′-Azobis(1<i>H</i>-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds |
| title_short | Structure and Thermal Properties of 2,2′-Azobis(1<i>H</i>-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds |
| title_sort | structure and thermal properties of 2 2 azobis 1 i h i imidazole 4 5 dicarbonitrile a promising starting material for a novel group of energetic compounds |
| topic | synthesis high-nitrogen materials thermal analysis azo compounds |
| url | https://www.mdpi.com/1420-3049/25/2/314 |
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