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

Faculty of Chemistry and Pharmacy, University of Innsbruck, 6020 Innsbruck, Austria
Institute of Mineralogy and Petrography, University of Innsbruck, 6020 Innsbruck, Austria
Author to whom correspondence should be addressed.
Academic Editor: Helmut Cölfen
Crystals 2016, 6(2), 20;
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)
PDF [9682 KB, uploaded 5 February 2016]


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

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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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