Computational Characterization of 2-Azidocycloalkanamines: Notional Variations on the Hypergol 2-Azido-N,N-Dimethylethanamine (DMAZ)

Report No. ARL-TR-2806
Authors: Michael J. McQuaid
Date/Pages: September 2002; 36 pages
Abstract: The fuel 2-azido-N,N-dimethylethanamine (DMAZ) has shown considerable promise as a replacement for hydrazine-based fuels in hypergolic propulsion systems, but the ignition delays observed for DMAZ-inhibited red fuming nitric acid (IRFNA) systems are longer than those for monomethylhydrazine-IRFNA systems. This report considers the potential of 2-azidodocycloalkanamine-based fuels for addressing this issue. Such molecules have two stereochemically distinct isomers, one of which prevents the azide group from "shielding" the amine lone pair electrons from proton attack. The other promotes such shielding. Since shielding likely influences the manner in which nitric acid reacts with amine-azide fuels, the ignition delays for the isomers may be different, and it is possible that one of the isomers will yield shorter ignition delays than DMAZ. To support consideration of the synthesis and development of 2-azido-N,N-dimethylcyclopropanamine (ADMCPA) equilibrium structures are identified and their gas-phase heats of formations estimated via density functional theory-based calculations. In addition, ADMCPA isomer condensed-phase densities and heats of vaporization are estimated via molecular dynamics simulations performed with halogen analogs. Combined and employed to predict ballistic properties, the computational results indicate that the ADMCPA isomers merit further investigation as hypergols. A suggestion for synthesizing cis?ADMCPA is also proffered.
Distribution: Approved for public release
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Last Update / Reviewed: September 1, 2002