Molecules 2014, 19(1), 896-910; doi:10.3390/molecules19010896
Article

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

1 State Key Laboratory of Explosion Science and Technology, School of Material Science & Engineering, Beijing Institute of Technology, Beijing 100081, China 2 Burning key laboratory, Xi'an Modern Chemistry Research Institute, Xi'an 710065, China
* Authors to whom correspondence should be addressed.
Received: 12 November 2013; in revised form: 6 January 2014 / Accepted: 8 January 2014 / Published: 14 January 2014
(This article belongs to the Special Issue Heterocyclic and Medicinal Chemistry)
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Abstract: 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 (1H, 13C, 15N), 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.
Keywords: energetic materials; detonation properties; azole-based compound; C-amino group; N-amino group

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MDPI and ACS Style

Zhao, X.; Qi, C.; Zhang, L.; Wang, Y.; Li, S.; Zhao, F.; Pang, S. Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties. Molecules 2014, 19, 896-910.

AMA Style

Zhao X, Qi C, Zhang L, Wang Y, Li S, Zhao F, Pang S. Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties. Molecules. 2014; 19(1):896-910.

Chicago/Turabian Style

Zhao, Xiuxiu; Qi, Cai; Zhang, Lubo; Wang, Yuan; Li, Shenghua; Zhao, Fengqi; Pang, Siping. 2014. "Amination of Nitroazoles — A Comparative Study of Structural and Energetic Properties." Molecules 19, no. 1: 896-910.

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