Assembling properties of 3,6-dinitropyrazolo-[4,3-c]pyrazole-based energetic compounds

被引:0
|
作者
Xinghui, Jin [1 ,3 ]
Fang, Yuan [1 ]
Yun, Shen [1 ]
Yufan, Liu [1 ]
Shengnan, Yao [1 ]
Shaochuan, Bai [1 ]
Bingcheng, Hu [2 ]
机构
[1] Qilu Univ Technol, Key Lab Fine Chem Univ Shandong, Shandong Acad Sci, Sch Chem & Chem Engn, Jinan, Peoples R China
[2] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing, Peoples R China
[3] Qilu Univ Technol, Key Lab Fine Chem Univ Shandong, Shandong Acad Sci, Sch Chem & Chem Engn, Jinan 250353, Peoples R China
关键词
3; 6-dinitropyrazolo-[4; 3-c]pyrazole; density functional theory; detonation properties; impact sensitivities; DENSITY-FUNCTIONAL THEORY; THEORY B3LYP METHOD; HIGH-LEVEL; HEATS; PERFORMANCE;
D O I
10.1002/poc.4469
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In pursuit of energetic materials with equal detonation properties and sensitivities compared to those of HMX and RDX, a series of 3,6-dinitropyrazolo-[4,3-c]pyrazole-based energetic compounds were designed, and density functional theory method was carried out to investigate the frontier molecular orbital, heats of formation, energetic properties, and impact sensitivities of the designed compounds. The results show that all the designed compounds possess high positive heats of formation range from 618.8 (A4) to 1934.3 kJ mol(-1) (E2) and the -N-3 energetic group was the most effective unit to improve the values of heats of formation. Values of oxygen balance of compounds E8 and F8 were zero and possess the most ideal oxygen balance. The calculated detonation properties indicate that the -C (NO2)(3) group was the most useful group to enhance the densities, detonation velocities, and detonation pressures. Nearly half of the designed compounds possess higher values of h(50) than RDX or HMX, which indicates that these compounds will be more stable than RDX and HMX. Based on detonation properties and impact sensitivities, five compounds (D3, D5, E5, F3, and F5) were screened as candidate compounds for high energy density materials. Finally, the distribution of the highest occupied molecular orbitals, the lowest unoccupied molecular orbitals, and electrostatic potential of the screened compounds were simulated to give an evident view on their physicochemical properties.
引用
收藏
页数:8
相关论文
共 50 条
  • [1] Thermally Stable 3,6-Dinitropyrazolo[4,3-c]pyrazole-based Energetic Materials
    Zhang, Jiaheng
    Parrish, Damon A.
    Shreeve, Jean'ne M.
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (10) : 2953 - 2960
  • [2] Synthesis and Properties of Novel Thermally Stable and Insensitive 3,6-dinitropyrazolo[4,3-c]pyrazole-based Energetic Materials
    Li, Yanan
    Chang, Pei
    Hu, Jianjian
    Chen, Tao
    Wang, Bin
    Wang, Yinglei
    Wang, Bozhou
    CURRENT ORGANIC CHEMISTRY, 2018, 22 (24) : 2407 - 2412
  • [3] Thermal studies of novel heat-resistant 3,6-dinitropyrazolo[4,3-c] pyrazole-based energetic materials
    Zhang, Yiying
    Zhai, Lianjie
    Xu, Cheng
    Chang, Pei
    Xu, Kangzhen
    Wang, Bozhou
    Li, Yanan
    JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 2023, 169
  • [4] 3,6-Dinitropyrazolo[4,3-c]pyrazole-Based Multipurpose Energetic Materials through Versatile N-Functionalization Strategies
    Yin, Ping
    Zhang, Jiaheng
    Mitchell, Lauren A.
    Parrish, Damon A.
    Shreeve, Jean'ne M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (41) : 12895 - 12897
  • [5] Curious cases of 3,6-dinitropyrazolo[4,3-c]pyrazole-based energetic cocrystals with high nitrogen content: an alternative to salt formation
    Zhang, Jiaheng
    Parrish, Damon A.
    Shreeve, Jean'ne M.
    CHEMICAL COMMUNICATIONS, 2015, 51 (34) : 7337 - 7340
  • [6] Synthesis and Properties of 3,6-Dinitropyrazolo[4,3-c]-pyrazole (DNPP) Derivatives
    Zhang, Wenquan
    Xia, Honglei
    Yu, Rujing
    Zhang, Jiaheng
    Wang, Kangcai
    Zhang, Qinghua
    PROPELLANTS EXPLOSIVES PYROTECHNICS, 2020, 45 (04) : 546 - 553
  • [7] Synthesis of Thermally Stable and Insensitive Energetic Materials by Incorporating the Tetrazole Functionality into a Fused-Ring 3,6-Dinitropyrazolo-[4,3-c]Pyrazole Framework
    Xia, Honglei
    Zhang, Wenquan
    Jin, Yunhe
    Song, Siwei
    Wang, Kangcai
    Zhang, Qinghua
    ACS APPLIED MATERIALS & INTERFACES, 2019, 11 (49) : 45914 - 45921
  • [8] Synthesis, structure and properties of neutral energetic materials based on N-functionalization of 3,6-dinitropyrazolo[4,3-c]pyrazole
    Li, Yanan
    Shu, Yuanjie
    Wang, Bozhou
    Zhang, Shengyong
    Zhai, Lianjie
    RSC ADVANCES, 2016, 6 (88) : 84760 - 84768
  • [9] Preparation and Thermal Decomposition Mechanism of 1,4-Diamino-3,6-dinitropyrazolo[4,3-c]pyrazole
    Li Y.-N.
    Hu J.-J.
    Chen T.
    Zhang Y.-Y.
    Wang B.
    Chang P.
    Wang B.-Z.
    Hanneng Cailiao/Chinese Journal of Energetic Materials, 2019, 27 (12): : 1025 - 1030
  • [10] Evaluating the effect of structural reorientation on thermochemical properties of 1,4-diamino-3,6-dinitropyrazolo[4,3-c]pyrazole
    Thungatha, Lamla
    Mahlase, Conrad
    Ngcebesha, Lisa
    SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2024, 78 : 54 - 60