Synthesis, LC-MS analysis and preliminary investigation of some properties of novel 1,3-dihydro-2H-benzimidazol-2-one nitro and nitramino derivatives

摘要

Synthesis and properties of series of novel 1,3-dihydro-2H-benzimidazol-2-one nitro and nitramino derivatives are described. The nitration reactions and purity of synthesized products were analyzed by LC-MS method. A detailed structure of one of the obtained compounds, 4,5,6-trinitro-1,3-dihydro-2H-benzimidazol-2-one (TriNBO) was characterized using low temperature (173 K) single crystal X-ray diffraction: orthorhombic yellow prism, space group 'P 2 21 21', experimental crystal density 1.767 g/cm~3 (at 173K). The TriNBO contains one activated nitrogroup in the 5-th position, which was used for the nucleophilic substitution in the aminolysis reactions with methylamine, ethylamine, n-propylamine and ethanolamine. The obtained aminoderivatives were nitrated with N2O5/ HNO3 and resulted a new group of appropriate nitramines: 1,3-dihydro-2H-5-R-N(NO2)-4,7-dinitrobenzimidazol-2-ones. These derivatives were investigated using LC-MS analysis and characterized by spectroscopical (UV, IR, 1H and 13C NMR methods). Thermal analysis (TGA) of three selected representatives was done. The most of new compounds possess a high melting points (200-315 °C) and thermal stability and can find a potential application as new thermostable energetic materials. Some calculated preliminary energetic characteristics show that TriNBO, 5-methylnitramino-1,3-dihydro-2H-4,7-dinitrobenzimidazol-2-one and 5-nitratoethylnitramino-1,3-dihydro-2H-4,7-dinitrobenzimidazol-2-one possess an increased energetic characteristics in comparisson with TNT. The proposed nitrocompounds may find a potential application as thermostable high energy materials.