Nitrotetrazolate-2<i>N</i>-oxides and the Strategy of <i>N</i>-Oxide Introduction GöbelMichael KaraghiosoffKonstantin KlapötkeThomas M. PierceyDavin G. StierstorferJörg 2010 The first anionic tetrazole-2<i>N</i>-oxide has been prepared by mild aqueous oxidation of easily prepared 5-nitrotetrazole with commercially available oxone in high yields. The result of protonating 5-nitrotetrazolate-2<i>N</i>-oxide has been identified as a hydroxytetrazole, and the nitrogen-rich salts including ammonium, hydroxylammonium, guanidinium, aminoguanidinum, diaminoguanidinium, and triaminoguanidinium have been prepared and characterized. When compared to the nitrogen-rich salts of nitrotetrazole, the nitrogen-rich salts of nitrotetrazole-2<i>N</i>-oxide show superior energetic performance as calculated by the EXPLO5 computer code, using heats of formation calculated using the CBS-4M level of quantum mechanical theory. The impact, friction, and electrical spark sensitivities of the nitrogen-rich nitrotetrazolate-2<i>N</i>-oxides were measured and cover the whole range from sensitive to insensitive energetic materials.