Investigations of the Vicarious C‐Aminations of 5,7‐Dinitrobenzotriazole and 4,6‐Dinitrobenzotriazol‐3‐ium‐1‐oxide and Their Energetic Properties |
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| Authors: | Dieter Ehlers Prof?Dr Thomas M Klapötke Carolin Pflüger |
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| Affiliation: | 1. Department of Physics, University of Augsburg, Universit?tsstrasse 1, 86135 Augsburg (Germany);2. Department of Chemistry, Ludwig Maximilian University of Munich (LMU), Butenandtstr. 5–13, 81377 Munich (Germany) |
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| 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 1H 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. |
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| Keywords: | amination EPR spectroscopy heterocycles oxides radicals zwitterions |
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