Nitrogen Homocycles Energetic Materials

The best known nitrogen homocyles are the pentazoles RN5. Phenylpentazole PhN5 is obtained as a thermally unstable compound by the reaction of benze-nediazonium chloride with lithium azide in methanol at —40°C [eqn (11.1)].  

The pentazolate anion. Ns (11.2), is estimated to have a half-life of 2.2 days, whereas that of the parent pentazole HN5 is predicted to be only ca 10 min in methanol at 0 Although HN5 is unknown, the cyclic anion N5 has been detected by tandem mass spectrometric studies of 4-hydroxyphenylpentazole. Similarly to its congener P5 (Section 11.2), N5 (isoelectronic with cyclopenta-dienide [C5H5] ) has the potential to form metallocene-like complexes. The acyclic (V-shaped) cation Ns has been isolated as a hexafluoroantimonate salt, which decomposes at ca 70 °C. The estimated energy density of [N5] [N5] is approximately twice that of hydrazine, a well-known rocket propellant, suggesting that this ionic polynitrogen allotrope would be an excellent monopropellant 

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