Dinitroacetylene: Can It be Made?

ABSTRACT With a predicted record‐high heat of formation, energy density, and outstanding performance as a rocket propellant, dinitroacetylene stretches the imagination for what is possible in terms of organic chemical explosives and monopropellants. In this study, we employ quantum chemical methods to predict its thermodynamic properties, ionization potential, electron affinity, ultraviolet‐visible spectra, nuclear magnetic resonance, and vibrational spectra, and to investigate proposed decomposition mechanisms. While unimolecular decomposition pathways are predicted to have high activation energies, nitrogen oxide radical species—commonly present in reaction mixtures of energetic materials—are found to significantly catalyze the decomposition of dinitroacetylene. This catalytic effect may explain previous unsuccessful synthesis attempts. A frontier orbital analysis suggests that partial reduction could increase the C─N bond order, offering a strategy to stabilize this elusive high‐energy‐density material.