A QSAR ANALYSIS OF SUBSTITUENT EFFECTS ON THE PHOTOINDUCED ACUTE TOXICITY OF PAHS

被引：101

作者：

VEITH, GD

MEKENYAN, OG

ANKLEY, GT

CALL, DJ

机构：

[1] UNIV WISCONSIN, LAKE SUPER RES INST, SUPERIOR, WI 54880 USA

[2] HIGHER INST CHEM TECHNOL, BU-8010 BURGAS, BULGARIA

来源：

CHEMOSPHERE | 1995年 / 30卷 / 11期

关键词：

D O I：

10.1016/0045-6535(95)00076-K

中图分类号：

X [环境科学、安全科学];

学科分类号：

08 ; 0830 ;

摘要：

Photoinduced toxicity of polycyclic aromatic hydrocarbons (PAHs) is a result of competing effects including stability and light absorbance of the molecules as well as irradiation parameters. The energy difference between the Highest Occupied Molecular Orbital and the Lowest Unoccupied Molecular Orbital (HOMO-LUMO gap), which can be computed directly from structure, was found to be the molecular descriptor that best distinguishes phototoxic chemicals from non-phototoxic chemicals. Aromatic chemicals that are phototoxic in sunlight have HOMO-LUMO gap energies that fall in the range of 6.7 to 7.5 eV. This study showed that the effect of most substituents on the HOMO-LUMO gap was negligible, and that phototoxicity in an aromatic chemical is likely only if the parent aromatic structure is phototoxic. Exceptions included substituents that add to delocalization (nitro and alkenyl) which could shift some chemicals with a HOMO-LUMO gap just above 7.5 eV into the domain of photoinduced toxicity.

引用

页码：2129 / 2142

页数：14

共 18 条

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