A Computationally Based Study of Polycyclic Nitramines and Their Precursors: Comparisons between Known and Notional Compounds

Report No. ARL-TR-7186
Authors: Michael J McQuaid; Chiung-Chu Chen
Date/Pages: February 2015; 132 pages
Abstract: A computationally based study was conducted to assess the potential viability of schemes proposed for employing cucurbiturils as precursors for the synthesis of polycyclic nitramines (PCNAs). One scheme involved reducing cucurbiturils to cucurbitaminals, then nitrolyzing them. The other involved hydrolyzing the cucurbiturils, then nitrating the secondary amine groups of the product. To assess the schemes' viabilities, an attempt was made to establish correlations between properties of equilibrium molecular structures and stability for known compounds, then employ the correlations to predict the stabilities of intermediates and targets. However, strong correlations were not found. Moreover, even if more evidence supporting hypothesized correlations had been found, results for the intermediates and targets of interest suggest that the yields of these schemes are likely to be low (at best) and that the targets will be unstable. The attempt to answer questions regarding the feasibility of producing PCNAs from cucurbiturils prompted the design and modeling of other notional PCNAs. Two appear to warrant further investigation. One is 2,6,7-trinitro-2,6,7-triaza[2.2.2]octane. It has a tris(nitramino) group. The other is a CL-20 analog with 4 >C(H)C(H)< groups and 4 nitramine groups.
Distribution: Approved for public release
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Last Update / Reviewed: February 1, 2015