Polynitro‐Functionalized Dipyrazolo‐1,3,5‐triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability
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.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Jun 19, 2017
- Source ID
- 10.1002/anie.201704687
Entities
People
- Damon A. Parrish
- Gregory H Imler
- Jean'ne Shreeve
- Jiaheng Zhang
- Ping Yin
Organizations
- Defense Threat Reduction Agency
- Harbin Institute of Technology
- M J Murdock Charitable Trust
- Office of Naval Research Global
- United States Naval Research Laboratory
- University of Idaho