Synthesis and reactivity of an unexpected highly sensitive 1-carboxymethyl-3-diazonio-5-nitrimino-1,2,4-triazole

Abstract

During the synthesis of functionalized energetic triazole derivatives for biosensor detection devices 1-carboxymethyl-3-diazonio-5-nitrimino-1,2,4-triazole (2) was obtained by nitration of sodium 1-carboxymethyl-3,5-diamino-1,2,4-triazole (1). Zwitterionic (2) behaves like a diazonium cation which was proved from its reaction with sodium azide by the formation of 3-azido-5-nitrimino-1,2,4-triazole (3). Compounds 1–3 were fully characterized by low temperature single crystal X-ray diffraction, vibrational (IR/Raman) spectroscopy, NMR spectroscopy, mass spectrometry, elemental analysis and DSC measurements. The sensitivities were determined by the BAM drop hammer, BAM friction tester and an electrostatic discharge device. The extremely high impact sensitivity of the diazonio compound in comparison to its azido analogue is explained by the use of electrostatic potentials.