Energetic salts based on nitroiminotetrazole-containing acetic acidElectronic supplementary information (ESI) available: NMR spectra. CCDC reference numbers 861469 (4H2O), 861471 (9), and 861470 (15). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c2jm30322a

2-(5-Nitroiminotetrazol-1-yl)acetic acid ( 4 ) was synthesized from 100% nitric acid and ethyl 2-(5-aminotetrazol-1-yl)acetate ( 2 ), which was easily obtained by reaction of ethyl aminoacetate hydrochloride, sodium hydroxide, and cyanogen azide. Compound 4 was also formed with 100% nitric acid and 2-(5-aminotetrazol-1-yl)acetic acid which was prepared from sodium 5-aminotetrazolate and 2-chloroacetic acid. New energetic materials comprised of nitroiminotetrazolate salts with nitroiminotetrazolate and carboxylate anions have been characterized spectroscopically as well as with single crystal X-ray diffraction and elemental analyses. In addition, the heats of formation ( H f ), and detonation pressures ( P ) and velocities ( D ) were calculated. All compounds were insensitive (>40 J) for impact with BAM Fallhammer. High density energetic salts containing nitrogen rich cations and 4-(carboxylatomethyl)-5-nitroiminotetrazol-1-ide have good calculated detonation properties for environmentally friendly explosive applications.