Development of a QSPR model for predicting thermal stabilities of nitroaromatic compounds taking into account their decomposition mechanisms

• Published in: Journal of molecular modeling Vol. 17; no. 10; pp. 2443 - 2453
• Main Authors: Fayet, Guillaume, Rotureau, Patricia, Joubert, Laurent, Adamo, Carlo
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer-Verlag 01.10.2011; Springer Verlag (Germany)
• Subjects: Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Computer Appl. in Life Sciences; Computer Applications in Chemistry; Engineering Sciences; Models, Chemical; Molecular Medicine; Molecular Structure; Nitro Compounds - chemistry; Original Paper; Quantitative Structure-Activity Relationship; Theoretical and Computational Chemistry; Thermodynamics; Quantitative structure–property relationship (QSPR); REACH regulation; Heat of decomposition; Density functional theory (DFT); Nitroaromatic compounds; NITROAROMATIC COMPOUNDS; DENSITY FUNCTIONAL THEORY (DFT); REACH REGULATION; QUANTITATIVE STRUCTURE-PROPERTY RELATIONSHIP (QSPR); HEAT OF DECOMPOSITION
• ISSN: 1610-2940; 0948-5023
• DOI: 10.1007/s00894-010-0908-0

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 (−Δ H ). 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.