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Screening benzylpentazoles for replacing PhN5 as cyclo-N5 precursor by theoretical calculation

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Abstract

Benzylpentazole (B) and its derivatives (B-NH 2  ~ B-NF 2 ) with electron-donating group (−NH2, −NHMe, −NMe2, and−OH) and electron-withdrawing group (−NO2, −CN, −CF3 and −NF2) were studied using density functional theory to assess their potentials for replacing phenylpentazole (PhN 5 ) as cyclo-N5 precursor. The pyrolysis mechanisms of the N5 ring and the C─N bond connecting pentazole and benzyl, bond lengths, and atomic charge have been investigated for revealing the effects of substituents on stability and assessing the possibilities of benzylpentazoles as cyclo-N5 precursor. Substituents especially electron-withdrawing groups lower the N5 ring stability and the C─N bond stability of B simultaneously. Compared to PhN 5 , benzylpentazoles mostly possess higher activation energy for the N5 ring decomposition (81.2 ~ 101.7 kJ/mol), lower C─N bond dissociation energy (385.6 ~ 452.8 kJ/mol), and higher chemical stability (7.83 ~ 8.49 eV). B and B-NMe 2 with the highest N5 ring stability, appropriate C─N bond stability, and chemical stability are the most potential candidates for replacing PhN 5 as cyclo-N5 precursor.

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Acknowledgements

The authors would like to acknowledge the Basic and Frontier Technical Research Project of Henan Province of China, No. 152300410228 and the University Innovation Team Project in Henan Province, No. 15IRTSTHN004.

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Correspondence to Xueli Zhang or Guoqun Liu.

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Zhang, X., Ma, C., Zhang, Y. et al. Screening benzylpentazoles for replacing PhN5 as cyclo-N5 precursor by theoretical calculation. Struct Chem 29, 267–274 (2018). https://doi.org/10.1007/s11224-017-1026-8

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Keywords

  • Benzylpentazoles
  • PhN5
  • Cyclo-N5 precursor
  • Group
  • Stability