Accession Number:

ADA613725

Title:

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

Descriptive Note:

Final rept. March 2013 July 2014

Corporate Author:

ARMY RESEARCH LAB ABERDEEN PROVING GROUND MD WEAPONS AND MATERIALS RESEARCH DIRECTORATE

Report Date:

2015-02-01

Pagination or Media Count:

132.0

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-triaza2.2.2octane. It has a trisnitramino group. The other is a CL-20 analog with 4 CHCH groups and 4 nitramine groups.

Subject Categories:

  • Physical Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE