title: Highly Energetic, Low Sensitivity Aromatic Peroxy Acids.
abstract: 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⋅⋅⋅O hydrogen bonds and numerous N⋅⋅⋅O, C⋅⋅⋅O, and O⋅⋅⋅O close contacts. These attractive lattice interactions may account for the less sensitive nature of 3,5-dinitrobenzoperoxoic acid.
authors.affiliation: Department of Chemistry, Wayne State University, Detroit, Michigan, 48202, USA.
authors.forename: Nipuni-Dhanesha H
authors.initials: ND
authors.lastname: Gamage
authors.affiliation: Department of Chemistry, Ludwig-Maximilians University, Butenandtstr. 5-13 (D), 81377, München, Germany.
authors.forename: Benedikt
authors.initials: B
authors.lastname: Stiasny
authors.affiliation: Department of Chemistry, Ludwig-Maximilians University, Butenandtstr. 5-13 (D), 81377, München, Germany.
authors.forename: Jörg
authors.initials: J
authors.lastname: Stierstorfer
authors.affiliation: Department of Chemistry, Wayne State University, Detroit, Michigan, 48202, USA.
authors.forename: Philip D
authors.initials: PD
authors.lastname: Martin
authors.affiliation: Department of Chemistry, Ludwig-Maximilians University, Butenandtstr. 5-13 (D), 81377, München, Germany. tmk@cup.uni-muenchen.de.
authors.forename: Thomas M
authors.initials: TM
authors.lastname: Klapötke
authors.affiliation: Department of Chemistry, Wayne State University, Detroit, Michigan, 48202, USA. chw@chem.wayne.edu.
authors.forename: Charles H
authors.initials: CH
authors.lastname: Winter
keywords: explosives; hydrogen bonding; peroxides; sensitivities; structure elucidation