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An Efficient Synthesis and Preliminary Investigation of Novel 1,3-Dihydro--benzimidazol-2-one Nitro and Nitramino Derivatives. | LitMetric

An Efficient Synthesis and Preliminary Investigation of Novel 1,3-Dihydro--benzimidazol-2-one Nitro and Nitramino Derivatives.

Materials (Basel)

Physics Faculty, Institute of Theoretical Physics and Astronomy, Vilnius University, Sauletekio av. 3, 01513 Vilnius, Lithuania.

Published: November 2022

The preparation and properties of a series of novel 1,3-dihydro--benzimidazol-2-one nitro and nitramino derivatives are described. A detailed crystal structure of one of the obtained compounds, 4,5,6-trinitro-1,3-dihydro--benzimidazol-2-one (TriNBO), was characterized using low temperature single crystal X-ray diffraction, namely an orthorhombic yellow prism, space group 'P 2 21 21', experimental crystal density 1.767 g/cm (at 173 K). Methyl analog, 5-Me-TriNBO-monoclinic red plates, space group, P 21/c, crystal density 1.82 g/cm. TriNBO contains one activated nitro group at the fifth position, which was used for the nucleophilic substitution in the aminolysis reactions with three monoalkylamines (R=CH, CH, (CH)CH) and ethanolamine. The 5-R-aminoderivatives were further nitrated with NO/ HNO and resulted in a new group of appropriate nitramines: 1,3-dihydro--5-R-N(NO)-4,6-dinitrobenzimidazol-2-ones. Thermal analysis (TGA) of three selected representatives was performed. The new compounds possess a high melting point (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-Me-TriNBO, 5-methylnitramino-1,3-dihydro--4,6-dinitrobenzimidazol-2-one, and 5-nitratoethylnitramino-1,3-dihydro--4,6-dinitrobenzimidazol-2-one possess increased energetic characteristics in comparison with TNT and tetryl. The proposed nitrocompounds may find potential applications as thermostable high-energy materials.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9737477PMC
http://dx.doi.org/10.3390/ma15238330DOI Listing

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