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Crystals 2016, 6(2), 20; doi:10.3390/cryst6020020

5-Azido-4-dimethylamino-1-methyl-1,2,4-triazolium Hexafluoridophosphate and Derivatives

1
Faculty of Chemistry and Pharmacy, University of Innsbruck, 6020 Innsbruck, Austria
2
Institute of Mineralogy and Petrography, University of Innsbruck, 6020 Innsbruck, Austria
*
Author to whom correspondence should be addressed.
Academic Editor: Helmut Cölfen
Received: 14 January 2016 / Revised: 1 February 2016 / Accepted: 2 February 2016 / Published: 5 February 2016
(This article belongs to the Special Issue Nitrogen-Rich Salts)
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Abstract

5-Azido-4-(dimethylamino)-1-methyl-1,2,4-triazolium hexafluoridophosphate was synthesized from the corresponding 5-bromo compound with NaN3. Reaction with bicyclo[2.2.1]hept-2-ene yielded a tricyclic aziridine, addition of an N-heterocyclic carbene resulted in a triazatrimethine cyanine, and reduction with triphenylphosphane gave the 5-amino derivative. The crystal structures of three nitrogen-rich salts were determined. Thermoanalysis of the cationic azide and triazene showed exothermal decomposition. The triazene exhibited negative solvatochromism in polar solvents involving the dipolarity π* and hydrogen-bond donor acidity α of the solvent. View Full-Text
Keywords: azide; aziridine; cyanine; solvatochromism; thermoanalysis; triazene; triazole azide; aziridine; cyanine; solvatochromism; thermoanalysis; triazene; triazole
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Laus, G.; Kahlenberg, V.; Schottenberger, H. 5-Azido-4-dimethylamino-1-methyl-1,2,4-triazolium Hexafluoridophosphate and Derivatives. Crystals 2016, 6, 20.

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