High density energetic salts containing nitrogen-rich cations and the nitranilic anion were readily synthesized in high yield by metathesis reactions of sodium nitranilate 2 and an appropriate halide. All of the new compounds were fully characterized by elemental, spectral (IR, (1)H, (13)C NMR), and thermal (DSC) analyses. The structure of hydrazinium nitranilate (4) was also determined by single-crystal X-ray analysis. The high symmetry and oxygen content of the anion give these salts extensive hydrogen bonding capability which further results in the high densities, low water solubilities, and high thermal stabilities (T(d)> 200 degrees C) of these compounds. Theoretical performance calculations were carried out by using Gaussian 03 and Cheetah 5.0. The calculated detonation pressures (P) for these new salts fall between 17.5 GPa (10) and 31.7 GPa (4), and the detonation velocities (nuD) range between 7022 m s(-1) (13) and 8638 m s(-1) (4).