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A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance
Design and synthesis of new compounds with both high detonation performances and good safety properties have always been a formidable task in the field of energetic materials. By introducing -ONO(2) and -NHNO(2) moieties into 1,2,4-oxadiazole- and 1,2,5-oxadiazole-based backbones, a new family of en...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Frontiers Media S.A.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7044674/ https://www.ncbi.nlm.nih.gov/pubmed/32154208 http://dx.doi.org/10.3389/fchem.2019.00942 |
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author | Xue, Qi Bi, Fu-qiang Zhang, Jun-lin Wang, Zi-jun Zhai, Lian-jie Huo, Huan Wang, Bo-zhou Zhang, Sheng-yong |
author_facet | Xue, Qi Bi, Fu-qiang Zhang, Jun-lin Wang, Zi-jun Zhai, Lian-jie Huo, Huan Wang, Bo-zhou Zhang, Sheng-yong |
author_sort | Xue, Qi |
collection | PubMed |
description | Design and synthesis of new compounds with both high detonation performances and good safety properties have always been a formidable task in the field of energetic materials. By introducing -ONO(2) and -NHNO(2) moieties into 1,2,4-oxadiazole- and 1,2,5-oxadiazole-based backbones, a new family of energetic materials, including ammonium 3-nitramino-4-(5-hydroxymethyl-1,2,4-oxadiazol-3-yl)-furazan (4), 3,3′-bis[5-nitroxymethyl-1,2,4-oxadiazol-3-yl]-4,4′-azofuroxan (6), [3-(4-nitroamino-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5-yl]-methylene nitrate (8), and its energetic ionic salts (10–12), were synthesized and fully characterized. The energetic and physical properties of the materials were investigated through theoretical calculations and experimental determination. The results show that the oxadiazole-based compounds exhibit high enthalpy of formations, good detonation performances, and extraordinary insensitivities. In particular, the hydrazinium salt (11) shows the best energetic properties (11: d = 1.821 g cm(−3); P = 35.1 GPa, v(D) = 8,822 m s(−1), IS = 40 J, FS > 360N). The ESP and Hirshfeld surface analysis indicated that a large number of hydrogen bonds as well as π-π stacking interactions within molecules might be the key reason for their low sensitivities and high energy-density levels. |
format | Online Article Text |
id | pubmed-7044674 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-70446742020-03-09 A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance Xue, Qi Bi, Fu-qiang Zhang, Jun-lin Wang, Zi-jun Zhai, Lian-jie Huo, Huan Wang, Bo-zhou Zhang, Sheng-yong Front Chem Chemistry Design and synthesis of new compounds with both high detonation performances and good safety properties have always been a formidable task in the field of energetic materials. By introducing -ONO(2) and -NHNO(2) moieties into 1,2,4-oxadiazole- and 1,2,5-oxadiazole-based backbones, a new family of energetic materials, including ammonium 3-nitramino-4-(5-hydroxymethyl-1,2,4-oxadiazol-3-yl)-furazan (4), 3,3′-bis[5-nitroxymethyl-1,2,4-oxadiazol-3-yl]-4,4′-azofuroxan (6), [3-(4-nitroamino-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5-yl]-methylene nitrate (8), and its energetic ionic salts (10–12), were synthesized and fully characterized. The energetic and physical properties of the materials were investigated through theoretical calculations and experimental determination. The results show that the oxadiazole-based compounds exhibit high enthalpy of formations, good detonation performances, and extraordinary insensitivities. In particular, the hydrazinium salt (11) shows the best energetic properties (11: d = 1.821 g cm(−3); P = 35.1 GPa, v(D) = 8,822 m s(−1), IS = 40 J, FS > 360N). The ESP and Hirshfeld surface analysis indicated that a large number of hydrogen bonds as well as π-π stacking interactions within molecules might be the key reason for their low sensitivities and high energy-density levels. Frontiers Media S.A. 2020-02-20 /pmc/articles/PMC7044674/ /pubmed/32154208 http://dx.doi.org/10.3389/fchem.2019.00942 Text en Copyright © 2020 Xue, Bi, Zhang, Wang, Zhai, Huo, Wang and Zhang. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Xue, Qi Bi, Fu-qiang Zhang, Jun-lin Wang, Zi-jun Zhai, Lian-jie Huo, Huan Wang, Bo-zhou Zhang, Sheng-yong A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance |
title | A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance |
title_full | A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance |
title_fullStr | A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance |
title_full_unstemmed | A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance |
title_short | A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance |
title_sort | family of energetic materials based on 1,2,4-oxadiazole and 1,2,5-oxadiazole backbones with low insensitivity and good detonation performance |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7044674/ https://www.ncbi.nlm.nih.gov/pubmed/32154208 http://dx.doi.org/10.3389/fchem.2019.00942 |
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