title: Quantitative structure-activity relationships of nitroaromatics toxicity to the algae (Scenedesmus obliguus).
abstract: The DFT-B3LYP method, with the basis set 6-311G( * *), was employed to calculate the molecular geometries and electronic structures of 25 nitroaromatics. The acute toxicity (-lgEC(50)) of these compounds to the algae (Scenedesmus obliguus) along with hydrophobicity described by logK(OW), and two quantum chemical parameters-energy of the lowest unoccupied molecular orbital, E(LUMO), and the charge of the nitro group, [ForQ(NO2), were used to establish the quantitative structure-activity relationships (QSARs). For 18 mononitro derivatives, the hydrophobicity parameter logK(OW) could interpret the toxic mechanism successfully. Dinitro aromatic compounds were susceptible to be reduced to aniline for their electrophilic nature. Their toxicity was controlled mainly by electronic factors instead of hydrophobicity. The electronic parameters, E(LUMO) and Q(NO2), were used to yield the following model: -lg EC(50) = 3.746 - 25.053 E(LUMO) + 6.481 Q(NO2) (n=22, R=0.926, SE=0.206, F=56.854, P<0.001). The predicted toxic values using the above equation are in good agreement with the experimental values.
authors.affiliation: Department of Chemistry, Nanjing University of Science and Technology, Nanjing 210094, PR China.
authors.forename: Xiu-Fen
authors.initials: XF
authors.lastname: Yan
authors.forename: He-Ming
authors.initials: HM
authors.lastname: Xiao
authors.forename: Xue-Dong
authors.initials: XD
authors.lastname: Gong
authors.forename: Xue-Hai
authors.initials: XH
authors.lastname: Ju
mesh_terms: D006841:Hydrocarbons, Aromatic / Q000737:chemistry / Q000633:toxicity*; D057927:Hydrophobic and Hydrophilic Interactions; D016014:Linear Models; D009574:Nitro Compounds / Q000737:chemistry / Q000633:toxicity*; D021281:Quantitative Structure-Activity Relationship; D044444:Scenedesmus / Q000187:drug effects*; D014874:Water Pollutants, Chemical / Q000633:toxicity*
chemical_list: D006841:Hydrocarbons, Aromatic; D009574:Nitro Compounds; D014874:Water Pollutants, Chemical