title: Investigations of the Vicarious C-Aminations of 5,7-Dinitrobenzotriazole and 4,6-Dinitrobenzotriazol-3-ium-1-oxide and Their Energetic Properties.
abstract: This combined experimental and theoretical study details the vicarious nucleophilic substitution by amination of 5,7-dinitrobenzotriazol (1) and 4,6-dinitrobenzotriazole-3-ium-1-oxide (4) with trimethylhydrazinium iodide to afford the new corresponding one- and two-time aminated compounds and investigations of its mechanism by EPR spectroscopy. The preferred position for the first amination is computed by spin density population and verified by X-ray crystallography. The zwitterionic structure of 4 is investigated in solution by (1) H NMR spectroscopy and in solid state by X-ray diffraction. Furthermore, the crystal structure of 1 is presented. The energetic behavior of the aminated products as well as the starting materials 1 and 4 was investigated, regarding sensitivities and performance.
authors.affiliation: Department of Physics, University of Augsburg, Universitätsstrasse 1, 86135 Augsburg (Germany).
authors.forename: Dieter
authors.initials: D
authors.lastname: Ehlers
authors.affiliation: Department of Chemistry, Ludwig Maximilian University of Munich (LMU), Butenandtstr. 5-13, 81377 Munich (Germany). tmk@cup.uni-muenchen.de.
authors.forename: Thomas M
authors.initials: TM
authors.lastname: Klapötke
authors.affiliation: Department of Chemistry, Ludwig Maximilian University of Munich (LMU), Butenandtstr. 5-13, 81377 Munich (Germany).
authors.forename: Carolin
authors.initials: C
authors.lastname: Pflüger
keywords: EPR spectroscopy; amination; heterocycles; oxides; radicals; zwitterions