6533b7dcfe1ef96bd1271e4e

RESEARCH PRODUCT

Molecular orbital studies on brominated diphenyl ethers. Part II—reactivity and quantitative structure–activity (property) relationships

Xionghui WeiReijo SuontamoÅKe BergmanEva JakobssonJiwei HuJuha KnuutinenErkki KolehmainenLars Eriksson

subject

Thyroid HormonesQuantitative structure–activity relationshipChromatography GasEnvironmental EngineeringHealth Toxicology and MutagenesisPolybrominated BiphenylsMolecular ConformationQuantitative Structure-Activity RelationshipEtherChemistry Techniques AnalyticalMass Spectrometrychemistry.chemical_compoundPolybrominated diphenyl ethersComputational chemistryAb initio quantum chemistry methodsEnvironmental ChemistryOrganic chemistryMolecular orbitalReactivity (chemistry)LuciferasesFlame RetardantsPhenyl EthersPublic Health Environmental and Occupational HealthRegioselectivityGeneral MedicineGeneral ChemistryPollutionchemistryElectrophile

description

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. � 2004 Elsevier Ltd. All rights reserved.

yearjournalcountryeditionlanguage
2005-05-01Chemosphere
https://doi.org/10.1016/j.chemosphere.2004.11.029