Triazidotrinitro Benzene: 1,3,5-(N3)3-2,4,6-(NO2)3C6

Triazidotrinitro benzene, 1,3,5-(N3)3-2,4,6-(NO2)3C6 (1) was synthesized by nitration of triazidodinitro benzene, 1,3,5-(N3)3-2,4-(NO2)2C6H with either a mixture of fuming nitric and concentrated sulfuric acid (HNO3/H2SO4) or with N2O5. Crystals were obtained by the slow evaporation of an acetone/acetic acid mixture at room temperature over a period of 2 weeks and characterized by single crystal X-ray diffraction: monoclinic, P 21/c (no. 14), a=0.54256(4), b=1.8552(1), c=1.2129(1) nm, β=94.91(1)°, V=1.2163(2) nm3, Z=4, ϱ=1.836 g⋅cm−3, Rall =0.069. Triazidotrinitro benzene has a remarkably high density (1.84 g⋅cm−3). The standard heat of formation of compound 1 was computed at B3LYP/6-31G(d, p) level of theory to be ΔH°f=765.8 kJ⋅mol−1 which translates to 2278.0 kJ⋅kg−1. The expected detonation properties of compound 1 were calculated using the semi-empirical equations suggested by Kamlet and Jacobs: detonation pressure, P=18.4 GPa and detonation velocity, D=8100 m⋅s−1.