Synthesis and characterization of the pentazolate anion cyclo -N 5 ˉ in (N 5 ) 6 (H 3 O) 3 (NH 4 ) 4 Cl

Pentazole (HN5), an unstable molecular ring comprising five nitrogen atoms, has been of great interest to researchers for the better part of a century. We report the synthesis and characterization of the pentazolate anion stabilized in a (N5)6(H3O)3(NH4)4Cl salt. The anion was generated by direct cleavage of the C-N bond in a multisubstituted arylpentazole using m-chloroperbenzoic acid and ferrous bisglycinate. The structure was confirmed by single-crystal x-ray diffraction analysis, which highlighted stabilization of the cyclo-N5- ring by chloride, ammonium, and hydronium. Thermal analysis indicated the stability of the salt below 117°C on the basis of thermogravimetry-measured onset decomposition temperature.