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

• Published in: Propellants, explosives, pyrotechnics Vol. 27; no. 1; pp. 7 - 11
• Main Authors: Adam, David, Karaghiosoff, Konstantin, Klapötke, Thomas M., Holl, Gerhard, Kaiser, Manfred
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag GmbH 01.03.2002; WILEY‐VCH Verlag GmbH
• ISSN: 0721-3115; 1521-4087
• DOI: 10.1002/1521-4087(200203)27:1<7::AID-PREP7>3.0.CO;2-J

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.