Prediction of Fenton oxidation positions in polycyclic aromatic hydrocarbons by Frontier electron density

Five recalcitrant polycyclic aromatic hydrocarbons (PAHs) in ethanol were subjected to Fenton oxidation, and following GC-MS identification of respective oxidation products, their oxidation positions were compared to those predicted by Frontier electron density. Quinone forms of oxidation products were identified in each PAH. With the exception of fluorene, oxidation positions of quinone forms of products of acenaphthylene, anthracene, benz(a)anthracene, and benzo(a)pyrene corresponded with predicted positions in which Frontier electron density was high. From these results, it appears that determining the Frontier electron density of a PAH is a promising method for predicting the Fenton oxidation position. (C) 2000 Elsevier Science Ltd. All rights reserved.