title: Amination of nitroazoles--a comparative study of structural and energetic properties.
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.
authors.affiliation: State Key Laboratory of Explosion Science and Technology, School of Material Science & Engineering, Beijing Institute of Technology, Beijing 100081, China. zhaoxiuxiu010@163.com.
authors.forename: Xiuxiu
authors.initials: X
authors.lastname: Zhao
authors.affiliation: State Key Laboratory of Explosion Science and Technology, School of Material Science & Engineering, Beijing Institute of Technology, Beijing 100081, China. qicaijingbei@163.com.
authors.forename: Cai
authors.initials: C
authors.lastname: Qi
authors.affiliation: State Key Laboratory of Explosion Science and Technology, School of Material Science & Engineering, Beijing Institute of Technology, Beijing 100081, China. xiaoahexiaob@163.com.
authors.forename: Lubo
authors.initials: L
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Explosion Science and Technology, School of Material Science & Engineering, Beijing Institute of Technology, Beijing 100081, China. invincibly@yeah.net.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Explosion Science and Technology, School of Material Science & Engineering, Beijing Institute of Technology, Beijing 100081, China. lishenghua@bit.edu.cn.
authors.forename: Shenghua
authors.initials: S
authors.lastname: Li
authors.affiliation: State Key Laboratory of Explosion Science and Technology, School of Material Science & Engineering, Beijing Institute of Technology, Beijing 100081, China. zhaofqi@163.com.
authors.forename: Fengqi
authors.initials: F
authors.lastname: Zhao
authors.affiliation: State Key Laboratory of Explosion Science and Technology, School of Material Science & Engineering, Beijing Institute of Technology, Beijing 100081, China. pangsp@bit.edu.cn.
authors.forename: Siping
authors.initials: S
authors.lastname: Pang
mesh_terms: D000586:Amination; D018360:Crystallography, X-Ray; D053834:Explosive Agents / Q000138:chemical synthesis*; D006834:Hydrazines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D011720:Pyrazoles / Q000138:chemical synthesis*; D013816:Thermodynamics; D014230:Triazoles / Q000138:chemical synthesis*
chemical_list: D053834:Explosive Agents; D006834:Hydrazines; D011720:Pyrazoles; D014230:Triazoles