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- Title
Polynitro-Functionalized Dipyrazolo-1,3,5-triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability.
- Authors
Yin, Ping; Zhang, Jiaheng; Imler, Gregory H.; Parrish, Damon A.; Shreeve, Jean'ne M.
- Abstract
A new fused N-heterocyclic framework, dipyrazolo-1,3,5-triazinane, was synthesized and the physiochemical properties of its derivatives were investigated to evaluate the integrated energetic performance. In contrast to 1,3,5-trinitro-1,3,5-triazinane (RDX) featuring a distorted chair confirmation, polynitro-functionalized dipyrazolo-1,3,5-triazinanes have nearly planar backbones, thereby enhancing the density and thermal stability. Among these new energetic tricyclic compounds, 5 a and 12 show favorable crystal densities of 1.937 g cm−3 and 1.990 g cm−3 at 150 K, respectively, which rank highest in triazinane-based energetic compounds. Additionally, this synthetic approach was carried out to form seven-membered and eight-membered rings, giving rise to tetranitro dipyrazolo-1,3,5-triazepane ( 5 b) and tetranitro dipyrazolo-1,3,5-triazocane ( 5 c), respectively.
- Subjects
ENERGY density; THERMAL stability; ALKYLATION kinetics; CRYSTAL structure; MOLECULAR structure of azoles
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 30, p8960
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201704687