title: On the prediction of thermal stability of nitroaromatic compounds using quantum chemical calculations.
abstract: This work presents a new approach to predict thermal stability of nitroaromatic compounds based on quantum chemical calculations and on quantitative structure-property relationship (QSPR) methods. The data set consists of 22 nitroaromatic compounds of known decomposition enthalpy (taken as a macroscopic property related to explosibility) obtained from differential scanning calorimetry. Geometric, electronic and energetic descriptors have been selected and computed using density functional theory (DFT) calculation to describe the 22 molecules. First approach consisted in looking at their linear correlations with the experimental decomposition enthalpy. Molecular weight, electrophilicity index, electron affinity and oxygen balance appeared as the most correlated descriptors (respectively R(2)=0.76, 0.75, 0.71 and 0.64). Then multilinear regression was computed with these descriptors. The obtained model is a six-parameter equation containing descriptors all issued from quantum chemical calculations. The prediction is satisfactory with a correlation coefficient R(2) of 0.91 and a predictivity coefficient R(cv)(2) of 0.84 using a cross validation method.
authors.affiliation: Laboratoire d'Electrochimie et Chimie Analytique, CNRS UMR-7575, Ecole Nationale Supérieure de Chimie de Paris, 75231 Paris Cedex 05, France.
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: D002152:Calorimetry, Differential Scanning / Q000379:methods; D002244:Carbon / Q000737:chemistry; D002621:Chemistry / Q000379:methods*; D004583:Electrons; D006358:Hot Temperature; D008956:Models, Chemical; D015233:Models, Statistical; D015394:Molecular Structure; D008970:Molecular Weight; D009584:Nitrogen / Q000737:chemistry; D017672:Nitrogen Compounds / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship; D011789:Quantum Theory; D012995:Solubility
chemical_list: D017672:Nitrogen Compounds; D002244:Carbon; D009584:Nitrogen; D010100:Oxygen