Theoretical exploration of the stabilities and detonation parameters of nitro-substituted 1H-benzotriazole

Lulin Li; Jiawei Zhang; Butong Li; Guobin Yi; Taoyu Wang; Yanhong Peng

doi:10.1007/s00894-024-05899-z

Theoretical exploration of the stabilities and detonation parameters of nitro-substituted 1H-benzotriazole

J Mol Model. 2024 Mar 14;30(4):104. doi: 10.1007/s00894-024-05899-z.

Authors

Lulin Li^{1

2

3}, Jiawei Zhang^{1

2}, Butong Li^{4

5

6}, Guobin Yi^{7

8}, Taoyu Wang^{1

2}, Yanhong Peng^{1

2}

Affiliations

¹ Guangdong Provincial Laboratory of Chemistry and Fine Chemical Engineering Jieyang Center, Jieyang, 522000, China.
² School of Advanced Manufacturing, Guangdong University of Technology, Jieyang, 510006, China.
³ School of Chemistry and Materials Science, Guizhou Education University, Guiyang, 051008, China.
⁴ Guangdong Provincial Laboratory of Chemistry and Fine Chemical Engineering Jieyang Center, Jieyang, 522000, China. butong.lee@gmail.com.
⁵ School of Advanced Manufacturing, Guangdong University of Technology, Jieyang, 510006, China. butong.lee@gmail.com.
⁶ School of Chemistry and Materials Science, Guizhou Education University, Guiyang, 051008, China. butong.lee@gmail.com.
⁷ Guangdong Provincial Laboratory of Chemistry and Fine Chemical Engineering Jieyang Center, Jieyang, 522000, China. yiguobin2023@outlook.com.
⁸ School of Advanced Manufacturing, Guangdong University of Technology, Jieyang, 510006, China. yiguobin2023@outlook.com.

PMID: 38483705
DOI: 10.1007/s00894-024-05899-z

Abstract

Context: The nitro group was introduced into the nitrogen heterocycle of 1H-benzotriazole to design a total of 31 derivatives. To estimate the thermal stability of these derivatives, the heat of formation (HOF) is calculated based on the isodesmic reaction. The bond dissociation energy (BDE) was also predicted based on the homolytic reaction to further evaluate the dynamic stability. To evaluate the possibility of utilizing as high energy density compounds (HEDCs), the detonation parameters including the detonation pressure (P), detonation velocity (D), and explosive heat (Q) are predicted by taking advantage of the Kamlet-Jacobs empirical equation. To measure the sensitivity to impact, both the characteristic height (H₅₀) and free space in crystal (∆V) are considered in this paper. Based on our calculations, D-series and E are found to be the candidates for HEDCs.

Methods: The Gaussian 09 software package was used in this paper. The B3PW91 hybrid function with the 6-311 + G(d,p) basis set was chosen to perform the structural optimization, frequency analysis, heat of formation, and bond dissociation energy. The detonation parameters were calculated following the Kamlet-Jacobs equation.

Keywords: 1H-benzotriazole; Density functional theory (DFT); High-energy-density compounds (HEDCs).