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An Advanced Heat-Resistant Explosive through Regional Isomerization and Intramolecular Integration

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    An Advanced Heat-Resistant Explosive through Regional Isomerization and Intramolecular Integration
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    • Chengchuang Li
      Chengchuang Li
      School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing 210094, P. R. China
      More by Chengchuang Li
    • Teng Zhu
      Teng Zhu
      School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing 210094, P. R. China
      More by Teng Zhu
    • Jie Tang
      Jie Tang
      School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing 210094, P. R. China
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    • Guangbin Cheng*
      Guangbin Cheng
      School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing 210094, P. R. China
      *Email: [email protected]
      More by Guangbin Cheng
      Orcidhttps://orcid.org/0000-0003-0501-6469
    • Chuan Xiao*
      Chuan Xiao
      China Northern Industries Group Co., Ltd. (NORINCO GROUP), Beijing 100089, P. R. China
      *Email: [email protected]
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    • Hongwei Yang*
      Hongwei Yang
      School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing 210094, P. R. China
      *Email: [email protected]
      More by Hongwei Yang
      Orcidhttps://orcid.org/0000-0003-4763-2972
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 13, 4505–4512
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    https://doi.org/10.1021/acs.joc.4c02048
    Published March 25, 2025
    Copyright © 2025 American Chemical Society
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    Abstract

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    Among all compounds constructed by intramolecular integration, 4 (Td = 321 °C, D = 8799 m s–1, IS = 35 J) that integrates ortho amino nitro group and tetrazole framework possesses a much better comprehensive performance than most widely used heat-resistant explosive HNS (Td = 318 °C, D = 7612 m s–1, IS = 5 J), which suggest that it might be a candidate for advanced heat-resistant explosive. Compared with 8, isomer 4 shows significant improvement in density, thermal stability and sensitivity, which may be caused by the relatively strong structural aromaticity, hydrogen bond and large face-to-face π–π interaction surfaces strength.

    Copyright © 2025 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.4c02048.

    • DSC plots of synthesized compounds, crystal structures and analysis of the obtained compounds are given in the Supporting Information (PDF)

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    Deposition Numbers 2354063–2354066 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via the joint Cambridge Crystallographic Data Centre (CCDC) and Fachinformationszentrum Karlsruhe Access Structures service.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 13, 4505–4512
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c02048
    Published March 25, 2025
    Copyright © 2025 American Chemical Society
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