Synthesis and Energetic Characterization of Borane-Amines on High-Nitrogen Heterocycles.

ABSTRACT

Borane-amines have garnered attention over the last several decades in a variety of applications, ranging from hydrogen storage materials to hypergolic fuel systems. An investigation into the synthesis of borane-amines with high-nitrogen content heterocycles was undertaken in this work. Borane-amines were formed by the reaction of BH3·Me2S in tetrahydrofuran (THF) with the requisite nitrogen-containing heterocycle and isolated by placing the crude reaction mixture in hexanes to precipitate the product. X-ray crystallography, thermogravimetric analysis (TGA), high resolution mass spectroscopy (HRMS), 1H NMR, 13C NMR, and 11B NMR were utilized for product characterization, while impact and friction sensitivity testing were conducted to identify sensitivity in the synthesized compounds. Most isolated borane-amines, except one, were found to decompose in the atmosphere and were more sensitive to mechanical stimuli than their starting materials; however, all synthesized compounds were found to be hypergolic in the presence of white fuming nitric acid (WFNA).