1,2,4‐Triazolium and Tetrazolium Picrate Salts: “On the Way” from Nitroaromatic to Azole‐Based Energetic Materials

Abstract

A family of energetic salts based on the picrate anion and several azolium cations were synthesized either by new methods or by known literature procedures. The cations of choice were the following: 5-amino-1H-tetrazolium (1), 5-amino-1-methyl-1H-tetrazolium (2), 5-amino-2-methyl-1H-tetrazolium (3), 5-amino-1,4-dimethyl-1H-tetrazolium (4), 5-amino-1,3-dimethyl-1H-tetrazolium (5), 1,5-diamino-1H-tetrazolium (6), 1,5-diamino-4-methyl-1H-tetrazolium (7), 3,4,5-triamino-1,2,4-triazolium or guanazinium (8) and 3,4,5-triamino-1-methyl-1,2,4-triazolium or methylguanazinium (9). A summary of the 15 N NMR shifts for all compounds is given, and the proton-/methyl-induced shifts (PISs/MISs) are discussed with relation to the crystal structures. Because hydrogen bonding plays an important role in determining the density and thus the performance of energetic materials, the crystal structures are discussed in detail. In addition, tests to

Study of picrate salts with amines

“…Calcd. (%) for C 7 Picric acid (0.22 g, 1.0 mmol) and cyclohexane 1,2-diamine (0.11 g, 0.5 mmol) were mixed in a water-methanol mixture (v/ v%, 1:4, 10 ml). The resulting solution was refluxed for 2 h and filtered through celite.…”

“…The crystal structures of picrate salts with amines have been studied in the past [6][7][8][9][10] but the mechanism of thermal analysis, explosion delay measurement are not yet reported in literature. When the picric acid is combined with amines, the resultant salts undergoes self propagative decomposition reaction due to the presence of both oxidizing (picric acid) and reducing (amines) groups in the same molecule.…”

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

“…[271,272]. Particularly in medicinal chemistry, the permanent positive charge rigid triazolium ring can easily form hydrogen bonds, accept electrons and produce electrostatic interaction with biological target sites leading to the enhancement of water solubility and membrane permeability, and thereby improving biological efficiency and broadening antimicrobial spectrum.…”

Synthesis, Structure, and Characterization of 3, 4′‐Bis‐1H‐1, 2,4‐triazolium Picrate Salt: A New High‐Energy Density Material

“…PA is a rich oxygen atom acid with strong oxidation, [23] which make it very easy to react with surroundings. [24] This makes picric acid a versatile agent. [25] TRTR molecule can show different coordination modes, such as monodentate, bidentate, chelating and bridged, while forming monomeric, dimeric, or polymeric structures.…”