Computational assessment of nitrogen-enriched, stable and insensitive tris(1,2,4,5-tetrazin-3-yl)amine building block for energetic applications

Abstract

In this work, we report an approach for designing a series of energetic compounds derived from nitrogen-rich tris(1,2,4,5-tetrazin-3-yl)amine backbone. Based on available synthetic method, nitrogen content (70.8%), heat of formation (1371 ​kJ·mol-1), density (1.67 ​g·cm-3), detonation parameters (7.75 ​km·s-1, 24.30 ​GPa), and experimentally reported high decomposition temperature (231 ​°C), less sensitivity to accidental impact (42 ​J) and friction (360 ​N) data, tris(1,2,4,5-tetrazin-3-yl)amine found to be an efficient building block for designing energetic materials. The explosophoric functional groups –NO2, –NH2, –ONO2, –NHNO2, and N3 were introduced in the tris(1,2,4,5-tetrazin-3-yl)amine framework to further improve energetic properties. All tris(1,2,4,5-tetrazin-3-yl)amine derivatives have a much higher heat of formation than TNT (2,4,6-trinitrotoluene) and RDX (1,3,5-trinitro-1,3,5-triazinane). Crucially, higher detonation velocities (>9.10 ​km·s-1) and detonation pressures (>35.20 ​GPa) were calculated for –NO2, –ONO2, and –NHNO2 substituted compounds compared to RDX. Considering the experimental and computed stability of tris(1,2,4,5-tetrazin-3-yl)amine towards high temperatures and mechanical stimuli, the entire designed molecules are expected to be less sensitive and stable for energetic applications. These advantages make tris(1,2,4,5-tetrazin-3-yl)amine an effective building block. There is no denying that the insertion of energetic functional groups will undoubtedly benefit the development of secondary explosives and propellants.

Keywords

• Tetrazine
• Energetic materials
• Sensitivity
• Detonation velocity
• Heat of formation