Synthesis, characterization, and thermal decomposition performance of 1,2,3-triazolyl-substituted 1,3,5-triazines with carbonyl, ester, and azide functional groups
Based on the organocatalytic reaction of enamine azide addition of 2,4,6-triazido-1,3,5-triazine to acetylacetone acetoacetic ester, we synthesized a series of previously unknown mono-, di-, and tri(1,2,3-triazolyl)-substituted-1,3,5-triazines that additionally carried carbonyl, ester, and azide gro...
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| Format: | Article |
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KeAi Communications Co. Ltd.
2023-12-01
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| Series: | Energetic Materials Frontiers |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666647223000672 |
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| author | Tat'yana V. Sokolnikova Maxim V. Penzik Alexey G. Proidakov Valery N. Kizhnyaev |
| author_facet | Tat'yana V. Sokolnikova Maxim V. Penzik Alexey G. Proidakov Valery N. Kizhnyaev |
| author_sort | Tat'yana V. Sokolnikova |
| collection | DOAJ |
| description | Based on the organocatalytic reaction of enamine azide addition of 2,4,6-triazido-1,3,5-triazine to acetylacetone acetoacetic ester, we synthesized a series of previously unknown mono-, di-, and tri(1,2,3-triazolyl)-substituted-1,3,5-triazines that additionally carried carbonyl, ester, and azide groups. The structure of the obtained compounds was proved by NMR (1H, 13C) and IR spectroscopy, and the composition was confirmed by elemental analysis. With the aid of differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) coupled to mass spectrometry (TG-MS), we obtained data on the thermal behavior and decomposition mechanism for these compounds. We demonstrated that di(1,2,3-triazolyl)-substituted 1,3,5-triazines have an increased thermal stability and have higher values of decomposition onset temperature (220–250 °C) in comparison with tri(1,2,3-triazolyl)-substituted 1,3,5-triazines (180 °C and 160 °C, respectively). |
| first_indexed | 2024-03-08T09:27:31Z |
| format | Article |
| id | doaj.art-06df80c1593d4e1aabaf68aeb853816f |
| institution | Directory Open Access Journal |
| issn | 2666-6472 |
| language | English |
| last_indexed | 2024-03-08T09:27:31Z |
| publishDate | 2023-12-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Energetic Materials Frontiers |
| spelling | doaj.art-06df80c1593d4e1aabaf68aeb853816f2024-01-31T05:45:43ZengKeAi Communications Co. Ltd.Energetic Materials Frontiers2666-64722023-12-0144213220Synthesis, characterization, and thermal decomposition performance of 1,2,3-triazolyl-substituted 1,3,5-triazines with carbonyl, ester, and azide functional groupsTat'yana V. Sokolnikova0Maxim V. Penzik1Alexey G. Proidakov2Valery N. Kizhnyaev3Faculty of Chemistry, Irkutsk State University, Irkutsk, 664003, RussiaFaculty of Chemistry, Irkutsk State University, Irkutsk, 664003, Russia; Melentiev Energy Systems Institute of Siberian Branch of the Russian Academy of Sciences, Irkutsk, 664033, Russia; Corresponding author. Melentiev Energy Systems Institute of Siberian Branch of the Russian Academy of Sciences, Irkutsk, 664033, Russia.Faculty of Chemistry, Irkutsk State University, Irkutsk, 664003, RussiaFaculty of Chemistry, Irkutsk State University, Irkutsk, 664003, RussiaBased on the organocatalytic reaction of enamine azide addition of 2,4,6-triazido-1,3,5-triazine to acetylacetone acetoacetic ester, we synthesized a series of previously unknown mono-, di-, and tri(1,2,3-triazolyl)-substituted-1,3,5-triazines that additionally carried carbonyl, ester, and azide groups. The structure of the obtained compounds was proved by NMR (1H, 13C) and IR spectroscopy, and the composition was confirmed by elemental analysis. With the aid of differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) coupled to mass spectrometry (TG-MS), we obtained data on the thermal behavior and decomposition mechanism for these compounds. We demonstrated that di(1,2,3-triazolyl)-substituted 1,3,5-triazines have an increased thermal stability and have higher values of decomposition onset temperature (220–250 °C) in comparison with tri(1,2,3-triazolyl)-substituted 1,3,5-triazines (180 °C and 160 °C, respectively).http://www.sciencedirect.com/science/article/pii/S2666647223000672Organic azide1,2,3-Triazole1,3,5-TriazineThermal behaviorTG-MS |
| spellingShingle | Tat'yana V. Sokolnikova Maxim V. Penzik Alexey G. Proidakov Valery N. Kizhnyaev Synthesis, characterization, and thermal decomposition performance of 1,2,3-triazolyl-substituted 1,3,5-triazines with carbonyl, ester, and azide functional groups Energetic Materials Frontiers Organic azide 1,2,3-Triazole 1,3,5-Triazine Thermal behavior TG-MS |
| title | Synthesis, characterization, and thermal decomposition performance of 1,2,3-triazolyl-substituted 1,3,5-triazines with carbonyl, ester, and azide functional groups |
| title_full | Synthesis, characterization, and thermal decomposition performance of 1,2,3-triazolyl-substituted 1,3,5-triazines with carbonyl, ester, and azide functional groups |
| title_fullStr | Synthesis, characterization, and thermal decomposition performance of 1,2,3-triazolyl-substituted 1,3,5-triazines with carbonyl, ester, and azide functional groups |
| title_full_unstemmed | Synthesis, characterization, and thermal decomposition performance of 1,2,3-triazolyl-substituted 1,3,5-triazines with carbonyl, ester, and azide functional groups |
| title_short | Synthesis, characterization, and thermal decomposition performance of 1,2,3-triazolyl-substituted 1,3,5-triazines with carbonyl, ester, and azide functional groups |
| title_sort | synthesis characterization and thermal decomposition performance of 1 2 3 triazolyl substituted 1 3 5 triazines with carbonyl ester and azide functional groups |
| topic | Organic azide 1,2,3-Triazole 1,3,5-Triazine Thermal behavior TG-MS |
| url | http://www.sciencedirect.com/science/article/pii/S2666647223000672 |
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