Quantum chemical studies on three novel 1,2,4-triazole N-oxides as potential insensitive high explosives

Abstract

Three novel explosives were designed by introducing N-oxides into 1,2,4-triazole: 1-amino-3,5-dinitro-1,2,4-triazole-2 N-oxide (ADT2NO), 1-amino-2,5-dinitro-1,2,4-triazole-3 N-oxide (ADT3NO), and 1-amino-3,5-dinitro-1,2,4-triazole-4 N-oxide (ADT4NO). Their detonation performance and sensitivity were estimated by using density functional theory and compared with some famous explosives like 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX) and 1-methyl-2,4,6-trinitrobenzene (TNT). All three designed molecules are more powerful than HMX and less sensitive than TNT, indicating that ADT2NO, ADT3NO, and ADT4NO have high detonation performance as HMX and low sensitivity as TNT, making them being very valuable and may be considered as the potential candidates of insensitive high explosives. Properly introducing N-oxides into the energetic triazole derivatives can generate some superior energetic compounds with both high explosive performance and reduced sensitivity.

Synthesis, Crystal Structure, and Thermal Behavior of 3‐(4‐Aminofurazan‐3‐yl)‐4‐(4‐nitrofurazan‐3‐yl)furazan (ANTF)

“…In order to obtain the heat of formation, the stable geometry of ANTF structure was fully optimized at B3LYP/6-31G** theoretical level [19] by using the Gaussian 09 program [20,21] and frequency calculations, and then the solid HOF was estimated by the relevant equation [22,23]. The detonation properties [detonation velocity (D) and detonation pressure (P)] were predicted according to HOF and the density by the Kamlet-Jacobs Equation [25]. The results indicate that HOF of ANTF is 562.36 kJ mol…”

“…To design and estimate an ovel explosive, the density and heat of formation( HOF) should be first considered.I no rder to obtain the heat of formation, the stable geometry of ANTF structure was fully optimized at B3LYP/6-31G** theoretical level [19] by using the Gaussian 09 program [20,21] and frequency calculations, and then the solid HOF wase stimated by the relevant equation [22,23].T he detonation properties [detonationv elocity( D)a nd detonation pressure (P)] were predicted according to HOF and the density by the Kamlet-Jacobs Equation [ 25].T he results indicate that HOF of ANTF is 562.36 kJ mol À1 .T he calculated values of D and P for ANTF are listed in Ta ble 7. Compared to other energetic materials [25][26][27],t he detonationv elocity of ANTF (D = 8.26 km s À1 )f alls in between TNT and TNAZ. Meanwhile, the impact sensitivity of ANTF is lower than DNTF,i ndicating that ANTF may be ap otential candidate of meltcast explosive.…”

“…Compared to other energetic materials [25][26][27], the detonation velocity of ANTF (D = 8.26 km s À1 ) falls in between TNT and TNAZ. Meanwhile, the impact sensitivity of ANTF is lower than DNTF, indicating that ANTF may be a potential candidate of meltcast explosive.…”

A Study of the Detonation Properties, Propellant Impulses, Impact Sensitivities and Synthesis of Nitrated ANTA and NTO Derivatives

“…Dipold et al nitrated ANTA to 5-nitramino-3-nitro-1,2,4-triazole which was found to be more impact and friction sensitive than RDX [5]. There have been several theoretical characterization studies of 1,2,4-triazole derivatives [6][7][8][9]. Turker and Atalar investigated 1,2,4-triazol-5-one where a nitro group was substituted at a carbon or nitrogen atom in the heterocycle [10].…”