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1,3,4‐Oxadiazole Bridges: A Strategy to Improve Energetics at the Molecular Level
Author(s) -
Ma Jinchao,
Chinnam Ajay Kumar,
Cheng Guangbin,
Yang Hongwei,
Zhang Jiaheng,
Shreeve Jean'ne M.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202014207
Subject(s) - oxadiazole , moiety , detonation velocity , detonation , explosive material , thermal stability , chemistry , reactivity (psychology) , materials science , crystal structure , computational chemistry , crystallography , organic chemistry , medicine , alternative medicine , pathology
Abstract Many energetic materials synthesized to date have limited applications because of low thermal and/or mechanical stability. This limitation can be overcome by introducing structural modifications such as a bridging group. In this study, a series of 1,3,4‐oxadiazole‐bridged furazans was prepared. Their structures were confirmed by 1 H and 13 C NMR, infrared, elemental, and X‐ray crystallographic analyses. The thermal stability, friction sensitivity, impact sensitivity, detonation velocity, and detonation pressure were evaluated. The hydroxylammonium salt 8 has an excellent detonation performance ( D =9101 m s −1 , P =37.9 GPa) and insensitive properties (IS=17.4 J, FS=330 N), which show its great potential as a high‐performance insensitive explosive. Using quantum computation and crystal structure analysis, the effect of the introduction of the 1,3,4‐oxadiazole moiety on molecular reactivity and the difference between the sensitivities and thermal stabilities of mono‐ and bis‐1,3,4‐oxadiazole bridges are considered. The synthetic method for introducing 1,3,4‐oxadiazole and the systematic study of 1,3,4‐oxadiazole‐bridged compounds provide a theoretical basis for future energetics design.