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A B3LYP and MP2(full) theoretical investigation into the strength of the C–NO2 bond upon the formation of the intermolecular hydrogen-bonding interaction between HF and the nitro group of nitrotriazole or its methyl derivatives

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Abstract

The changes of bond dissociation energy (BDE) in the C–NO2 bond and nitro group charge upon the formation of the intermolecular hydrogen-bonding interaction between HF and the nitro group of 14 kinds of nitrotriazoles or methyl derivatives were investigated using the B3LYP and MP2(full) methods with the 6-311++G**, 6-311++G(2df,2p) and aug-cc-pVTZ basis sets. The strength of the C–NO2 bond was enhanced and the charge of nitro group turned more negative in complex in comparison with those in isolated nitrotriazole molecule. The increment of the C–NO2 bond dissociation energies correlated well with the intermolecular H-bonding interaction energies. Electron density shifts analyses showed that the electron density shifted toward the C–NO2 bond upon complex formation, leading to the strengthened C–NO2 bond and the possibly reduced explosive sensitivity.

C1-N2 bond turns strong upon H-bond formation, leading to a possibly reduced explosive sensitivity

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Linyi University, Linyi, 276005, China

    Bao-Hui Li

  2. The Third Hospital of Shanxi Medical University, Taiyuan, 030053, China

    Wen-jing Shi

  3. College of Chemical Engineering and Environment, North University of China, Taiyuan, 030051, China

    Fu-de Ren & Yong Wang

Authors
  1. Bao-Hui Li
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  2. Wen-jing Shi
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  3. Fu-de Ren
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  4. Yong Wang
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Correspondence to Wen-jing Shi or Fu-de Ren.

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Li, BH., Shi, Wj., Ren, Fd. et al. A B3LYP and MP2(full) theoretical investigation into the strength of the C–NO2 bond upon the formation of the intermolecular hydrogen-bonding interaction between HF and the nitro group of nitrotriazole or its methyl derivatives. J Mol Model 19, 511–519 (2013). https://doi.org/10.1007/s00894-012-1574-1

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  • DOI: https://doi.org/10.1007/s00894-012-1574-1

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