Theoretical design of new bridge-ring insensitive high energy compounds by selected normal Diels-Alder reactions between NH_(2)-substituted oxazoles and NO_(2)/NF_(2)/NHNO_(2)-substituted ethylenes/acetylenes  

作　　者：Qiong Wu Qin-nan Hu Ming-quan Li Ze-wu Zhang Wei-hua Zhu 

机构地区：[1]Jiangsu Key Laboratory of Advanced Structural Materials and Application Technology,School of Materials Science and Engineering,Nanjing Institute of Technology,1 Hongjing Road,Nanjing,211167,China [2]Institute for Computation in Molecular and Materials Science and Department of Chemistry,Nanjing University of Science and Technology,Nanjing,210094,China

出　　处：《Defence Technology（防务技术）》2021年第5期1731-1739,共9页Defence Technology

基　　金：the Natural Science Foundation of Jiangsu(BK20170761);Natural Science Foundation of Nanjing Institute of Technology(JCYJ201806);Science Innovation Project for Undergraduates of Nanjing Institute of Technology(TB202002005);Outstanding Scientific and Technological Innovation Team in Colleges and Universities of Jiangsu Province,and Jiangsu Overseas Visiting Scholar Program for University Prominent Young&Middle-aged Teachers and Presidents.

摘　　要：In this work,NH_(2)-substituted oxazoles and NO_(2)/NF_(2)/NHNO_(2)-substituted ethylenes/acetylenes were designed and used as dienes and dienophiles,respectively,in order to develop new bridge-ring insensitive high energy compounds through the Diels-Alder reaction between them.The reaction type,reaction feasibility and performance of reaction products were investigated in detail theoretically.The results showed that dienes most possibly react with dienophiles through the HOMO-diene controlled normal Diels-Alder reaction at relatively low energy barrier.Tetranitroethylene could react with the designed dienes much more easily than other dienophiles,and was employed to further design 29 new bridge-ring energetic compounds.Due to high heat of formation,density and oxygen balance,all designed bridge-ring energetic compounds have outstanding detonation performance,16 of them have higher energy than HMX(1,3,5,7-tetranitro-1,3,5,7-tetrazocine)and 2 others even possess comparative energy with the representative of high energy compounds CL-20(2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane).The predicted average h50 value of these bridge-ring energetic compounds is 83 cm,showing their low impact sensitivity.The NH2 groups could obviously impel the proceeding of Diels-Alder reactions,but would slightly decrease the energy and sensitivity performance.In all,the new designed bridge-ring compounds have both high energy and low sensitivity,and may be produced through Diels-Alder reactions at relatively low energy barrier.This paper may be helpful for the theoretical design and experiment synthesis of new advanced insensitive high energy compounds.

关 键 词：Diels-Alder Energetic compounds OXAZOLE High energy Insensitive 

分 类 号：TQ560.1[化学工程—炸药化工]