Asymmetric fluorodinitromethyl derivatives of 2,2,2-trinitroethyl N-(2,2,2-trinitroethyl)carbamate

The energetic polynitro compounds 2,2,2-trinitroethyl 2,2,2-trinitroethylcarbamate, 2-fluoro-2,2-dinitroethyl 2,2,2-trinitroethylcarbamate, 2,2,2-tinitroethyl 2-fluoro-2,2-dinitroethylcarbamate and 2-fluoro-2,2-dinitroethyl 2,2,2-trinitroethylcarbonate were synthesized and investigated as potential high energy dense oxidizers. Due to their structural similarity, the compounds have been compared with each other by using various analytical methods, like single-crystal X-ray diffraction, vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis, mass spectrometry and multi-temperature DSC measurements. The suitability of the compounds as potential oxidizers in energetic formulations has been investigated. In addition, the heats of formation of the products were calculated with the program package Gaussian 09. Several detonation parameters such as the detonation pressure, velocity, energy and temperature were computed using the EXPLO5 code. Furthermore, the sensitivity toward impact, friction and electrical discharge was tested using a BAM drop hammer, a friction tester as well as a small-scale electrical discharge device.