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Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties

In this work, 3-nitro-1H-1,2,4-triazole (1) and 3,5-dinitro-1H-pyrazole (2) were C-aminated and N-aminated using different amination agents, yielding their respective C-amino and N-amino products. All compounds were fully characterized by NMR ((1)H, (13)C, (15)N), IR spectroscopy, differential scann...

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Autores principales: Zhao, Xiuxiu, Qi, Cai, Zhang, Lubo, Wang, Yuan, Li, Shenghua, Zhao, Fengqi, Pang, Siping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272014/
https://www.ncbi.nlm.nih.gov/pubmed/24424403
http://dx.doi.org/10.3390/molecules19010896
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author Zhao, Xiuxiu
Qi, Cai
Zhang, Lubo
Wang, Yuan
Li, Shenghua
Zhao, Fengqi
Pang, Siping
author_facet Zhao, Xiuxiu
Qi, Cai
Zhang, Lubo
Wang, Yuan
Li, Shenghua
Zhao, Fengqi
Pang, Siping
author_sort Zhao, Xiuxiu
collection PubMed
description In this work, 3-nitro-1H-1,2,4-triazole (1) and 3,5-dinitro-1H-pyrazole (2) were C-aminated and N-aminated using different amination agents, yielding their respective C-amino and N-amino products. All compounds were fully characterized by NMR ((1)H, (13)C, (15)N), IR spectroscopy, differential scanning calorimetry (DSC). X-ray crystallographic measurements were performed and delivered insight into structural characteristics as well as inter- and intramolecular interactions of the products. Their impact sensitivities were measured by using standard BAM fallhammer techniques and their explosive performances were computed using the EXPLO 5.05 program. A comparative study on the influence of those different amino substituents on the structural and energetic properties (such as density, stability, heat of formation, detonation performance) is presented. The results showed that the incorporation of an N-amino group into a nitroazole ring can improve nitrogen content, heat of formation and impact sensitivity, while the introduction of a C-amino group can enhance density, detonation velocity and pressure. The potential of N-amino and C-amino moieties for the design of next generation energetic materials is explored.
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spelling pubmed-62720142018-12-20 Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties Zhao, Xiuxiu Qi, Cai Zhang, Lubo Wang, Yuan Li, Shenghua Zhao, Fengqi Pang, Siping Molecules Article In this work, 3-nitro-1H-1,2,4-triazole (1) and 3,5-dinitro-1H-pyrazole (2) were C-aminated and N-aminated using different amination agents, yielding their respective C-amino and N-amino products. All compounds were fully characterized by NMR ((1)H, (13)C, (15)N), IR spectroscopy, differential scanning calorimetry (DSC). X-ray crystallographic measurements were performed and delivered insight into structural characteristics as well as inter- and intramolecular interactions of the products. Their impact sensitivities were measured by using standard BAM fallhammer techniques and their explosive performances were computed using the EXPLO 5.05 program. A comparative study on the influence of those different amino substituents on the structural and energetic properties (such as density, stability, heat of formation, detonation performance) is presented. The results showed that the incorporation of an N-amino group into a nitroazole ring can improve nitrogen content, heat of formation and impact sensitivity, while the introduction of a C-amino group can enhance density, detonation velocity and pressure. The potential of N-amino and C-amino moieties for the design of next generation energetic materials is explored. MDPI 2014-01-14 /pmc/articles/PMC6272014/ /pubmed/24424403 http://dx.doi.org/10.3390/molecules19010896 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Zhao, Xiuxiu
Qi, Cai
Zhang, Lubo
Wang, Yuan
Li, Shenghua
Zhao, Fengqi
Pang, Siping
Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties
title Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties
title_full Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties
title_fullStr Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties
title_full_unstemmed Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties
title_short Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties
title_sort amination of nitroazoles — a comparative study of structural and energetic properties
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272014/
https://www.ncbi.nlm.nih.gov/pubmed/24424403
http://dx.doi.org/10.3390/molecules19010896
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