5,5',6,6'-Tetranitro-2,2'-bibenzimidazole: A Thermally Stable and Insensitive Energetic Compound

Łukasz Gutowski; Waldemar Trzciński; Mateusz Szala

doi:10.1002/cplu.201700541

5,5',6,6'-Tetranitro-2,2'-bibenzimidazole: A Thermally Stable and Insensitive Energetic Compound

Chempluschem. 2018 Feb;83(2):87-91. doi: 10.1002/cplu.201700541.

Authors

Łukasz Gutowski¹, Waldemar Trzciński¹, Mateusz Szala¹

Affiliation

¹ Department of Explosives, Military University of Technology, 2 Kaliskiego Street, 00-908, Warsaw, Poland.

PMID: 31957307
DOI: 10.1002/cplu.201700541

Abstract

A new energetic compound, namely a secondary explosive (5,5',6,6'-tetranitro-2,2'-bibenzimidazole, TNBBI) with high thermal stability is described. TNBBI is synthesized through direct nitration of 2,2'-bibenzimidazole with nitric acid. TNBBI decomposes exothermically at 394 °C without visible melting. The heat of combustion and the standard enthalpy of formation are determined experimentally. The detonation parameters calculated for the new compound are slightly lower than those for TNT. However, the combination of TNBBI's high decomposition temperature and low sensitivity make it a promising thermally stable energetic compound. The structure of the new compound is confirmed by NMR and IR spectroscopy.

Keywords: NMR spectroscopy; bibenzimidazole; energetic materials; hydrogen bonds; nitration; synthesis.