Insight into shock-induced chemical reaction from the perspective of ring strain and rotation of chemical bonds

Bisheng Tan, Xinping Long, Jinshan Li, Fude Nie, Jinglun Huang

科研成果: 期刊稿件文献综述同行评审

15 引用 (Scopus)

摘要

Density functional theory BLYP/DNP and hyperhomodesmotic equations were employed to calculate ring strain energy, the bond dissociation energy of X-NO2 (X0C, N) and the charges on the nitro groups of several fourmembered and six-membered heterocycle compounds. BLYP/DNP and LST/QST + CG method were also applied to calculate bond rotational energy of X-NO2 (X0C, N) of above mentioned compounds. It indicated that ring strain energy of four-membered heterocycle nitro compounds is apparently higher than that of six-membered heterocycle nitro compounds. Predictably, ring-opening reactions may preferentially occur for those compounds containing higher ring strain energy under shock. In addition, C-NO2 bonds in these compounds may rotate easier than N-NO2 bonds in response to the external shock. As for N-NO2 bonds in these compounds, they also respond to the external shock by the rotation of N-NO2 bonds, once to the saddle point of the rotational energy barrier, the whole molecule will become relaxed, N- NO 2 bond becomes weaker and eventually leads to the breakage. When one -C0O, -C0NH or -NH2 group is introduced to the six-membered heterocycle, the charges on the nitro groups of the new compound decrease drastically, and ring strains increase remarkably. It can be predicted that the new compounds will bemore sensitive to shock, and the viewpoint is confirmed by the experimental results of shock sensitivity (small scale gap test) of several explosives.

源语言英语
页(从-至)5127-5132
页数6
期刊Journal of Molecular Modeling
18
12
DOI
出版状态已出版 - 12月 2012
已对外发布

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