TY - JOUR
T1 - A comparative study of bridged 1,2,4-oxazolones and their derivatives
AU - Fei, Teng
AU - Sun, Chenghui
AU - He, Chunlin
AU - Pang, Siping
N1 - Publisher Copyright:
© 2020 The Authors
PY - 2020/6/25
Y1 - 2020/6/25
N2 - For energetic compounds, a slight difference in their molecular structures can result in a tremendous difference in their properties. Compounds with similar structures but exhibiting big difference in their physicochemical properties (such as density and detonation properties) are of interest to the researchers. The understanding of the reason causes the difference in their properties is important for designing new energetic compounds with improved performances. In this study, the structural and physicochemical properties of 3,3′-bis-1,2,4-oxadiazole-5,5′-dione (1) and 3,3′-azo-1,2,4-oxadiazole-5,5′-dione (2) and their derivatives were presented. All of the synthesized compounds were fully characterized, the comparative studies showed that 1 and its ionic derivatives were found to exhibit higher detonation velocities and pressures as well as higher densities than their corresponding azo linkage analogs. The crystal structures for the two neutral compounds were compared by Hirshfeld surface and non-covalent interaction analyses. The results indicate that a high packing coefficient and extensive π-π stacking interactions are two major reasons for 1 exhibiting better physicochemical and energetic properties.
AB - For energetic compounds, a slight difference in their molecular structures can result in a tremendous difference in their properties. Compounds with similar structures but exhibiting big difference in their physicochemical properties (such as density and detonation properties) are of interest to the researchers. The understanding of the reason causes the difference in their properties is important for designing new energetic compounds with improved performances. In this study, the structural and physicochemical properties of 3,3′-bis-1,2,4-oxadiazole-5,5′-dione (1) and 3,3′-azo-1,2,4-oxadiazole-5,5′-dione (2) and their derivatives were presented. All of the synthesized compounds were fully characterized, the comparative studies showed that 1 and its ionic derivatives were found to exhibit higher detonation velocities and pressures as well as higher densities than their corresponding azo linkage analogs. The crystal structures for the two neutral compounds were compared by Hirshfeld surface and non-covalent interaction analyses. The results indicate that a high packing coefficient and extensive π-π stacking interactions are two major reasons for 1 exhibiting better physicochemical and energetic properties.
KW - 1,2,4-Oxazolone
KW - Crystal structure
KW - Detonation performance
KW - Energetic compounds
UR - http://www.scopus.com/inward/record.url?scp=85116632843&partnerID=8YFLogxK
U2 - 10.1016/j.enmf.2020.06.001
DO - 10.1016/j.enmf.2020.06.001
M3 - Article
AN - SCOPUS:85116632843
SN - 2666-6472
VL - 1
SP - 26
EP - 33
JO - Energetic Materials Frontiers
JF - Energetic Materials Frontiers
IS - 1
ER -