Systematic Synthesis of Thermally Stable Zwitterionic Energetic Materials Based on 4-Hydroxy-3,5-dinitropyrazole

4-Hydroxy-3,5-dinitropyrazole (HODNP) was investigated as a precursor for synthesizing two thermally stable, insensitive zwitterionic energetic materials. The ability of the hydroxy functionality to carry negative charge was leveraged and further covalently bonded with two positively charged moieties (3,4-diamino-1,2,4-triazole and acetimidamide) via N-functionalization to form zwitterions <b>2</b> and <b>3</b>. Structural characterization and a study of the energetic performance were carried out. The zwitterionic nature of compound <b>3</b> was confirmed by single-crystal analysis.