Substituent effects on detonation properties and stability of energetic dipicrylamine derivatives from a theoretical study

ABSTRACT

Density functional theory calculations were performed to look for potential energetic materials and discuss the effects of various substituents (NO₂, CN, NH₂, N₃, NHNO₂ and ONO₂) on the detonation performance and stability of thirty dipicrylamine (DPA) derivatives. It is found that the number of substituents has little effect on the molecular densities, detonation velocities, and detonation pressures for CN, N₃, and NH₂ derivatives, while these quantities show a gradually increasing trend with the number of substituents growing in NHNO₂, NO₂, and ONO₂ series molecules. Moreover,3,5-diazido-N-(3-azido-2,4,6-trinitrophenyl)-2,4,6-trinitroaniline (B4), bis(3,5-diazido-2,4,6-trinitrophenyl)amine (B5), N,N'-(2,4,6-trinitro-5-((2,4,6-trinitrophenyl)amino)-1,3-phenylene)dinitramide (D2), N,N'-(azanediylbis(2,4,6-trinitro-3,1-phenylene))dinitramide (D3), N,N'-(2,4,6-trinitro-5-((2,4,6-trinitro-3-(nitroamino)phenyl)amino)-1,3-phenylene)dinitramide (D4), N,N’,N'‘,N'''-(azanediylbis(2,4,6-trinitrobenzene-5,1,3-triyl))tetranitramide (D5), 2,3,4,5,6-pentanitro-N-(2,3,4,6-tetranitrophenyl)aniline (E4), bis(2,3,4,5,6-pentanitrophenyl)amine (E5), 2,4,6-trinitro-5-((2,4,6-trinitrophenyl)amino)-1,3-phenylene dinitrate (F2), azanediylbis(2,4,6-trinitro-3,1-phenylene) dinitrate (F3) possess higher explosive power values than RDX. Furthermore, the BDEs of all derivatives are remarkably larger than that of RDX, and the h₅₀ of mostly designed molecules is larger than that of CL-20. Due to the good detonation performance and stability, D4, D5, and E5 are recommended as potential energetic materials.

KEYWORDS:

• High energy density compounds
• density functional theory
• detonation performance
• K-J equations

Acknowledgments

This work was supported by the Henan Provincial Science and Technology Foundation (No: 202102210236), Natural Science Foundation of Henan Province (No: 202300410155), and the National Natural Science Foundation of China (No: 21006057).

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by the Henan Provincial Science and Technology Foundation [grant number 202102210236], Natural Science Foundation of Henan Province [grant number 202300410155], and the National Natural Science Foundation of China [grant number 21006057].