caa a22 4500 605513384 CHVBK 20210128100700.0 cr unu---uuuuu 210128e20150501xx s 000 0 eng 10.1007/s00894-015-2653-x doi (NATIONALLICENCE)springer-10.1007/s00894-015-2653-x A theoretical study on the strength of the C-NO2 bond and ring strain upon the formation of the intermolecular H-bonding interaction between HF and nitro group in nitrocyclopropane, nitrocyclobutane, nitrocyclopentane or nitrocyclohexane [Elektronische Daten] [Wei Qiu, Fu-de Ren, Wen-jing Shi, Yan-hong Wang] As a follow-up to our investigation into the influence of H-bond on the C-NO2 trigger bond, a comparison of the effect of the H-bond on the ring strain energy with the C-NO2 bond dissociation energy was carried out in the HF complex with nitrocyclopropane, nitrocyclobutane, nitrocyclopentane, and nitrocyclohexane by using the DFT-B3LYP and MP2 (full) methods with the 6-311++G(2df,2p) and aug-cc-pVTZ basis sets. The C-NO2 bond length decreases with strengthening of trigger-bond while the ring perimeter increases companied by weakening of ring strain upon the complex formation. The H-bonding energy correlates well with the increment of ring perimeter and the change of ring bond angle. For nitrocyclopropane∙∙∙HF, the effect of H-bond on the ring strain energy is notable, while for the other complex, it is negligible. Therefore, for nitrocyclopropane∙∙∙HF, the origin of the change of explosive sensitivity might be due to the increment of the C-NO2 bond dissociation energy and decrease of the ring strain energy, while for the other complex, it might be only due to the strengthening of C-NO2 bond. The analysis of electron density shifts shows that the C-C bond in ring loses density while the C-NO2 bond gains density, leading to the weakened ring strain and strengthened C-NO2 bond, and thus the possibly reduced explosive sensitivity. Graphical Abstract For the nitrocyclopropane complex with HF, the origin of sensitivity change is due to the increment of the BDE in C-NO2 bond and decrease of the ring strain energy, while for the other complex it is only due to the strengthening of C-NO2 bond. Springer-Verlag Berlin Heidelberg, 2015 Bond dissociation energy nationallicence Intermolecular H-bond nationallicence MP2 (full) nationallicence Ring strain nationallicence Sensitivity nationallicence Qiu Wei State Key Laboratory of Urban Water Resource and Enviroment, Harbin Institute of Technology, 150001, Harbin, China aut Ren Fu-de College of Chemical Engineering and Environment, North University of China, 030051, Taiyuan, China aut Shi Wen-jing The Third Hospital of Shanxi Medical University, 030053, Taiyuan, China aut Wang Yan-hong College of Chemical Engineering and Environment, North University of China, 030051, Taiyuan, China aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/5(2015-05-01), 1-9 1610-2940 21:5<1 2015 21 894 https://doi.org/10.1007/s00894-015-2653-x text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2653-x text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Qiu Wei State Key Laboratory of Urban Water Resource and Enviroment, Harbin Institute of Technology, 150001, Harbin, China aut NATIONALLICENCE 700 1- Ren Fu-de College of Chemical Engineering and Environment, North University of China, 030051, Taiyuan, China aut NATIONALLICENCE 700 1- Shi Wen-jing The Third Hospital of Shanxi Medical University, 030053, Taiyuan, China aut NATIONALLICENCE 700 1- Wang Yan-hong College of Chemical Engineering and Environment, North University of China, 030051, Taiyuan, China aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/5(2015-05-01), 1-9 1610-2940 21:5<1 2015 21 894