Isomers matter in energetic materials

Abstract

Unlike chemists who make drugs, fragrances, and agrochemicals, chemists who make energetic materials, like explosives and propellants, don’t spend much time worrying about stereo- and regiochemistry. Their thinking is that the precise arrangement of substituents on a compound doesn’t really matter if they’re going to blow it up or burn it. But that logic is all wrong, say researchers at CCDC US Army Research Laboratory and Scripps Research in California. They report that differences in stereo- and regiochemistry can result in energetic molecules with vastly different physical properties (J. Am. Chem. Soc. 2019, DOI: 10.1021/jacs.9b06961). The group, led by the Army Research Lab’s Jesse J. Sabatini and Scripps’s Phil S. Baran, synthesized all six stereo- and regioisomers of a cyclobutyl compound with four nitrate ester substituents (shown). Computations suggested that the compounds’ explosive properties would be similar to one another and just a little better than the explosive TNT. From