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Gamage, Nipuni-Dhanesha H.; Stiasny, Benedikt; Stierstorfer, Jörg; Martin, Philip D.; Klapötke, Thomas M.; Winter, Charles H. (2016): Highly Energetic, Low Sensitivity Aromatic Peroxy Acids. In: Chemistry-A European Journal, Vol. 22, No. 8: 2582-
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The synthesis, structure, and energetic materials properties of a series of aromatic peroxy acid compounds are described. Benzene-1,3,5-tris(carboperoxoic) acid is a highly sensitive primary energetic material, with impact and friction sensitivities similar to those of triacetone triperoxide. By contrast, benzene-1,4-bis(carboperoxoic) acid, 4-nitrobenzoperoxoic acid, and 3,5-dinitrobenzoperoxoic acid are much less sensitive, with impact and friction sensitivities close to those of the secondary energetic material 2,4,6-trinitrotoluene. Additionally, the calculated detonation velocities of 3,5-dinitrobenzoperoxoic acid and 2,4,6-trinitrobenzoperoxoic acid exceed that of 2,4,6-trinitrotoluene. The solid-state structure of 3,5-dinitrobenzoperoxoic acid contains intermolecular O-H center dot center dot center dot O hydrogen bonds and numerous N center dot center dot center dot O, C center dot center dot center dot O, and O center dot center dot center dot O close contacts. These attractive lattice interactions may account for the less sensitive nature of 3,5-dinitrobenzoperoxoic acid.