title: Structure-Activity Relationship Analysis of the Thermal Stabilities of Nitroaromatic Compounds Following Different Decomposition Mechanisms.
abstract: The decomposition behavior of energetic materials is very important for the safety problems concerning their production, transportation, use and storage, because molecular decomposition is intimately connected to their explosive properties. Nitroaromatic compounds, particularly nitrobenzene derivatives, are often considered as prototypical energetic molecules, and some of them are commonly used as high explosives. Quantitative structure-activity relationship (QSAR) represents a potential tool for predicting the thermal stability properties of energetic materials. But it is reported that constructing general reliable models to predict their stability and their potential explosive properties is a very difficult task. In this work, we make our efforts to investigate the relationship between the molecular structures and corresponding thermal stabilities of 77 nitrobenzene derivatives with various substituent functional groups (in ortho, meta and/or para positions). The proposed best MLR model, developed by the new software QSARINS, based on Genetic Algorithm for variable selection and with various validation tools, is robust, stable and predictive with R(2) of 0.86, QLOO (2) of 0.79 and CCC of 0.90. The results indicated that, though difficult, it is possible to build predictive, externally validated QSAR models to estimate the thermal stability of nitroaromatic compounds.
authors.affiliation: School of Pharmacy, Lanzhou University, Donggang West Road 199, 730000 Lanzhou, P. R. China tel: +86-931-8915686; fax: +86-931-8915686. lijiazhong@lzu.edu.cn.
authors.forename: Jiazhong
authors.initials: J
authors.lastname: Li
authors.affiliation: School of Pharmacy, Lanzhou University, Donggang West Road 199, 730000 Lanzhou, P. R. China tel: +86-931-8915686; fax: +86-931-8915686.
authors.forename: Huanxiang
authors.initials: H
authors.lastname: Liu
authors.affiliation: Department of Chemistry, Lanzhou University, Tianshui South Road 222, 730000 Lanzhou, P. R. China.
authors.forename: Xing
authors.initials: X
authors.lastname: Huo
authors.affiliation: QSAR Research Unit in Environmental Chemistry and Ecotoxicology, Department of Theoretical and Applied Sciences, University of Insubria via Dunant 3, 21100 Varese, Italy http://www.qsar.it.
authors.forename: Paola
authors.initials: P
authors.lastname: Gramatica
keywords: External validation parameters; Heat of decomposition; Nitroaromatic compounds; Quantitative StructureActivity Relationship (QSAR)