Theoretical Evaluation Of Substituted
Polycyclic Aromatic Hydrocarbons
As Emerging Pollutant Phototoxins
Author(s)
K. Rowberg, N. Nataraj, W. Saroian & L. Kang
Abstract
Phototoxicity potential was predicted for 88 substituted PAHs. The geometry of
all PAHs was optimized and the molecular orbital energies were calculated using
AM1 Hamiltonian. The highest occupied molecular orbital energy (EHOMO) and
the lowest unoccupied molecular orbital energy (ELUMO) were used to calculate
the energy gap (EHOMO−ELUMO). The energy gap was used to predict
phototoxicity for chloro-, bromo-, nitro- and methyl-substituted PAHs. Of the 88
compounds in the study, only nitro substituents on carbazole were predicted to
induce phototoxicity of the nonphototoxic parent.
Keywords: polycyclic aromatic hydrocarbons, PAH, phototoxicity, HOMOLUMO
gap, emerging pollutants.
1 Introduction
Polycyclic aromatic hydrocarbons (PAHs) are planar, nonpolar, semi-volatile
chemical compounds that are composed of two or more fused aromatic rings.
PAHs originate from point sources (e.g. oil spills, industrial processes [1] and
fossil fuel combustion) or non-point source pollutants (e.g. atmospheric
deposition, road runoff, forest fires, and volcanoes). Rain may move PAHs
deposited on the soil to the groundwater. Although PAHs have low aqueous
solubility, they readily adsorb on sediment of the groundwater. Phase equilibria
between sediment and water and mass transfer controls the release of PAHs from
nonaqueous phase liquids or sediment into the aqueous phase. Although PAHs
are formed primarily as by-products of carbonaceous fuel consumption, PAHs
Keywords
polycyclic aromatic hydrocarbons, PAH, phototoxicity, HOMOLUMO
gap, emerging pollutants.
Related Book
Other papers in this volume
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