title: Development of a QSPR model for predicting thermal stabilities of nitroaromatic compounds taking into account their decomposition mechanisms.
abstract: The molecular structures of 77 nitroaromatic compounds have been correlated to their thermal stabilities by combining the quantitative structure-property relationship (QSPR) method with density functional theory (DFT). More than 300 descriptors (constitutional, topological, geometrical and quantum chemical) have been calculated, and multilinear regressions have been performed to find accurate quantitative relationships with experimental heats of decomposition (-ΔH). In particular, this work demonstrates the importance of accounting for chemical mechanisms during the selection of an adequate experimental data set. A reliable QSPR model that presents a strong correlation with experimental data for both the training and the validation molecular sets (R (2) = 0.90 and 0.84, respectively) was developed for non-ortho-substituted nitroaromatic compounds. Moreover, its applicability domain was determined, and the model's predictivity reached 0.86 within this applicability domain. To our knowledge, this work has produced the first QSPR model, developed according to the OECD principles of regulatory acceptability, for predicting the thermal stabilities of energetic compounds.
authors.affiliation: Institut National de l'Environnement Industriel et des Risques (INERIS), Parc Technologique Alata, BP2, 60550 Verneuil-en-Halatte, France. guillaume.fayet@ineris.fr
authors.forename: Guillaume
authors.initials: G
authors.lastname: Fayet
authors.forename: Patricia
authors.initials: P
authors.lastname: Rotureau
authors.forename: Laurent
authors.initials: L
authors.lastname: Joubert
authors.forename: Carlo
authors.initials: C
authors.lastname: Adamo
mesh_terms: D008956:Models, Chemical; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship; D013816:Thermodynamics
chemical_list: D009574:Nitro Compounds