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

Molecules

Xiuxiu Zhao¹  Cai Qi¹  Lubo Zhang¹  Yuan Wang¹  Shenghua Li¹  Fengqi Zhao² 

[1] State Key Laboratory of Explosion Science and Technology, School of Material Science & Engineering, Beijing Institute of Technology, Beijing 100081, China; E-Mails:;Burning key laboratory, Xi’an Modern Chemistry Research Institute, Xi’an 710065, China; E-Mail:

关键词: energetic materials;    detonation properties;    azole-based compound;    C-amino group;    N-amino group;   

DOI  :  10.3390/molecules19010896

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.