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Gamage ND, Stiasny B, Stierstorfer J, et al. Highly Energetic, Low Sensitivity Aromatic Peroxy Acids. Chemistry. 2016;22(8):2582-5doi: 10.1002/chem.201502989.
Gamage, N. D., Stiasny, B., Stierstorfer, J., Martin, P. D., Klapötke, T. M., & Winter, C. H. (2016). Highly Energetic, Low Sensitivity Aromatic Peroxy Acids. Chemistry (Weinheim an der Bergstrasse, Germany), 22(8), 2582-5. https://doi.org/10.1002/chem.201502989
Gamage, Nipuni-Dhanesha H, et al. "Highly Energetic, Low Sensitivity Aromatic Peroxy Acids." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,8 (2016): 2582-5. doi: https://doi.org/10.1002/chem.201502989
Gamage ND, Stiasny B, Stierstorfer J, Martin PD, Klapötke TM, Winter CH. Highly Energetic, Low Sensitivity Aromatic Peroxy Acids. Chemistry. 2016 Feb 18;22(8):2582-5. doi: 10.1002/chem.201502989. Epub 2016 Jan 07. PMID: 26743434.
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Chemistry. 2016 Feb 18;22(8):2582-5. doi: 10.1002/chem.201502989. Epub 2016 Jan 07.

Highly Energetic, Low Sensitivity Aromatic Peroxy Acids.

Chemistry (Weinheim an der Bergstrasse, Germany)

Nipuni-Dhanesha H Gamage, Benedikt Stiasny, Jörg Stierstorfer, Philip D Martin, Thomas M Klapötke, Charles H Winter

Affiliations

  1. Department of Chemistry, Wayne State University, Detroit, Michigan, 48202, USA.
  2. Department of Chemistry, Ludwig-Maximilians University, Butenandtstr. 5-13 (D), 81377, München, Germany.
  3. Department of Chemistry, Ludwig-Maximilians University, Butenandtstr. 5-13 (D), 81377, München, Germany. [email protected].
  4. Department of Chemistry, Wayne State University, Detroit, Michigan, 48202, USA. [email protected].

PMID: 26743434 DOI: 10.1002/chem.201502989

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.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: explosives; hydrogen bonding; peroxides; sensitivities; structure elucidation

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