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 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.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Sep 23, 2015
- Source ID
- 10.1002/chem.201502812
Entities
People
- Carolin Pflüger
- Dieter Ehlers
- Thomas M. Klapötke
Organizations
- Konrad Adenauer Foundation
- Ludwig-Maximilians-Universität München
- Office of Naval Research
- United States Army Research Laboratory