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Updated: May 5, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Transition metal complexes of 3-amino-1-nitroguanidine as laser ignitible primary explosives: structures and
Niko Fischer1, Manuel Joas, Thomas M Klapötke
1Energetic Materials Research, Department of Chemistry, University of Munich (LMU) , Butenandtstrasse 5-13, D-81377, Germany.
Abstract:
3-Amino-1-nitroguanidine (ANQ, 2) was synthesized via hydrazinolysis of nitroguanidine. By dissolving 2 in solutions containing transition metal salts, several complexes M(2+)(ANQ)2X2(H2O)y with M(2+) = Co, Ni, Cu, Zn as well as M(ANQ)2X(H2O)y with M = Ag could be isolated. In these cases, nitrate as well as perchlorate and chloride served as the respective anions X. Additionally, the ANQ complexes of Co, Ni, and Ag with dinitramide as the anion were synthesized from ANQ and silver dinitramide and by reacting the cobalt and nickel ANQ perchlorate complexes with ammonium dinitramide. The crystal structures of all described complexes were determined by low temperature single-crystal X-ray diffraction. Additionally, they were characterized using IR spectroscopy and elemental analysis. The decomposition temperatures were determined by differential scanning calorimetry and the sensitivities toward impact and friction were assessed using a BAM drophammer and a BAM friction tester (BAM = Bundesanstalt für Materialforschung und -prüfung). Additionally, the sensitivity toward electrostatic discharge was determined on a small-scale ESD device. The potential use of the nitrate, dinitramide and perchlorate containing species as primary explosives was investigated in a laser ignition test.
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