Energetic Sila-Nitrocarbamates: Silicon Analogues of Neo-Pentane Derivatives

Four silanes based on the neo-pentane skeleton Me4‑xSi­(CH2R)x containing carbamate groups (x = 1–4, R = OC­(O)­NH2) have been prepared via the corresponding alcohols Me4–xSi­(CH2OH)x, starting from the chlorosilanes Me4–xSiClx. Subsequent nitration leads to the corresponding primary nitrocarbamates (R = OC­(O)­NHNO2), examined for the purpose as potential energetic materials, including the silicon analogue of pentaerythritol tetranitrocarbamate (sila-PETNC) and a siloxane based nitrocarbamate side-product. All compounds were thoroughly characterized by spectroscopic methods including X-ray diffraction. Thermal stabilities and sensitivities toward impact and friction were examined, as well as detonation values by calculating energies of formation using the EXPLO5 V6.02 software.