Structure/property relationships of a new high-nitrogen, energetic heterocycle: The role of the cation in triazolo-aminotriazinyltetrazinate salt sensitivity

ORGN 642

David M. Rosenberg, RosenbergDM@ih.navy.mil1, Peter Politzer, ppolitze@uno.edu2, and J. S. Murray2. (1) Research and Technology, Indian Head Division, Naval Surface Warfare Center, 101 Strauss Ave, Indian Head, MD 20640, (2) Dept. of Chemistry, University of New Orleans, New Orleans, LA 70148
A recently synthesized heterocycle (1), derived from the diazotization of an amino triazole fused to a diaminotriazine, has the unusual properties of being a strong acid and an energetic compound. Its anion can be viewed as a “cloaked azide”. Salts derived from the neutralization of 1 with high-nitrogen bases are of particular interest as candidate materials in propellant compositions. The sensitivity characteristics of salts derived from triaminoguanidine, diaminoguanidine, ammonia, hydrazine, dihydrazino tetrazine, as well as various metal salts and 1 itself were examined experimentally and computationally. Densities, heats of formation, sensitivity data (impact, friction, ESD), calculated structures, electrostatic charge distributions, and cohesive energies will be reported. Rationalization of observed trends relating structure and sensitivity, distinct from that utilized for nitro-arenes, nitramines, or even other high nitrogen heterocycles will be presented.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005