Investigations of the Vicarious C‐Aminations of 5,7‐Dinitrobenzotriazole and 4,6‐Dinitrobenzotriazol‐3‐ium‐1‐oxide and Their Energetic Properties
Publication type: Journal Article
Publication date: 2015-09-23
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
26397388
General Chemistry
Catalysis
Organic Chemistry
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.
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14
Total citations:
14
Citations from 2025:
1
(7.14%)
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Ehlers D., Klapötke T. M., Pflüger C. Investigations of the Vicarious C‐Aminations of 5,7‐Dinitrobenzotriazole and 4,6‐Dinitrobenzotriazol‐3‐ium‐1‐oxide and Their Energetic Properties // Chemistry - A European Journal. 2015. Vol. 21. No. 45. pp. 16073-16082.
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Ehlers D., Klapötke T. M., Pflüger C. Investigations of the Vicarious C‐Aminations of 5,7‐Dinitrobenzotriazole and 4,6‐Dinitrobenzotriazol‐3‐ium‐1‐oxide and Their Energetic Properties // Chemistry - A European Journal. 2015. Vol. 21. No. 45. pp. 16073-16082.
Cite this
RIS
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TY - JOUR
DO - 10.1002/chem.201502812
UR - https://doi.org/10.1002/chem.201502812
TI - Investigations of the Vicarious C‐Aminations of 5,7‐Dinitrobenzotriazole and 4,6‐Dinitrobenzotriazol‐3‐ium‐1‐oxide and Their Energetic Properties
T2 - Chemistry - A European Journal
AU - Ehlers, Dieter
AU - Klapötke, Thomas M.
AU - Pflüger, Carolin
PY - 2015
DA - 2015/09/23
PB - Wiley
SP - 16073-16082
IS - 45
VL - 21
PMID - 26397388
SN - 0947-6539
SN - 1521-3765
ER -
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BibTex (up to 50 authors)
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@article{2015_Ehlers,
author = {Dieter Ehlers and Thomas M. Klapötke and Carolin Pflüger},
title = {Investigations of the Vicarious C‐Aminations of 5,7‐Dinitrobenzotriazole and 4,6‐Dinitrobenzotriazol‐3‐ium‐1‐oxide and Their Energetic Properties},
journal = {Chemistry - A European Journal},
year = {2015},
volume = {21},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/chem.201502812},
number = {45},
pages = {16073--16082},
doi = {10.1002/chem.201502812}
}
Cite this
MLA
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Ehlers, Dieter, et al. “Investigations of the Vicarious C‐Aminations of 5,7‐Dinitrobenzotriazole and 4,6‐Dinitrobenzotriazol‐3‐ium‐1‐oxide and Their Energetic Properties.” Chemistry - A European Journal, vol. 21, no. 45, Sep. 2015, pp. 16073-16082. https://doi.org/10.1002/chem.201502812.