Impact of Stereo- and Regiochemistry on Energetic Materials

The synthesis, physical properties and calculated performances of six stereo- and regioisomeric cyclobutane nitric ester materials is described. While the calculated performances of these isomers, as expected, were similar, their physical properties were found to be extremely different. By altering the stereo- and regiochemistry, complete tunability in the form of low-or high-melting solids, standalone melt-castable explosives, melt-castable explosive eutectic compounds, and liquid propellant materials were obtained. This study demonstrates that theoretical calculations should not be the main factor in driving the design and synthesis of new materials, and that stereo- and regiochemistry offer a new dimension to consider when designing compounds of potential relevance to energetic formulators.