title: Molecular orbital studies on brominated diphenyl ethers. Part II--reactivity and quantitative structure-activity (property) relationships.
abstract: Polybrominated diphenyl ethers (PBDEs) are widely used as flame retardants and are increasingly turning up in the environment. Their structural similarities to polychlorinated biphenyls and thyroid hormones suggest they may be a risk to human health. The present study examines the reactivity of brominated diphenyl ethers (BDEs) on the basis of the electronic structures as calculated by semiempirical AM1 self-consistent field molecular orbital (SCF-MO) method. Frontier orbital energies were used to elucidate the reactivity of BDEs in electrophilic, nucleophilic and photolytic reactions. From an examination of the frontier electron densities, the regioselectivity, or orientation, of metabolic reactions of BDEs was predicted. Furthermore, satisfactory quantitative structure-activity (property) relationship (QSAR and QSPR) models were derived to calculate gas chromatographic and ultraviolet spectral properties and luciferase induction activities from the AM1-computed electronic parameters.
authors.affiliation: Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Peking University, 100871 Beijing, PR China.
authors.forename: Jiwei
authors.initials: J
authors.lastname: Hu
authors.forename: Lars
authors.initials: L
authors.lastname: Eriksson
authors.forename: Ake
authors.initials: A
authors.lastname: Bergman
authors.forename: Eva
authors.initials: E
authors.lastname: Jakobsson
authors.forename: Erkki
authors.initials: E
authors.lastname: Kolehmainen
authors.forename: Juha
authors.initials: J
authors.lastname: Knuutinen
authors.forename: Reijo
authors.initials: R
authors.lastname: Suontamo
authors.forename: Xionghui
authors.initials: X
authors.lastname: Wei
mesh_terms: D002623:Chemistry Techniques, Analytical / Q000379:methods*; D002849:Chromatography, Gas; D005411:Flame Retardants; D008156:Luciferases / Q000378:metabolism; D013058:Mass Spectrometry; D008968:Molecular Conformation; D010647:Phenyl Ethers / Q000737:chemistry* / Q000378:metabolism; D011075:Polybrominated Biphenyls / Q000737:chemistry* / Q000378:metabolism; D021281:Quantitative Structure-Activity Relationship; D013963:Thyroid Hormones / Q000378:metabolism
chemical_list: D005411:Flame Retardants; D010647:Phenyl Ethers; D011075:Polybrominated Biphenyls; D013963:Thyroid Hormones; D008156:Luciferases