How Do the Partitioning Properties of Polyhalogenated POPs Change When Chlorine Is Replaced with Bromine?

Abstract

Information about the mobility and the partitioning properties of brominated persistent organic pollutants, the environmental levels of which are sometimes higher than those of the chlorinated analogues, is limited. We estimated n-octanol/water (log KOW), n-octanol/air (log KOA), and air/water (log KAW) partition coefficients for 1436 chloro- and bromo-analogues of dibenzo-p-dioxins, dibenzofurans, biphenyls, naphthalenes, diphenyl ethers, and benzenes by employing quantitative structure−property relationship (QSPR) techniques. The searches for similar partitioning patterns were performed by means of two-dimensional cluster analysis. Five classes of compounds were identified. Each of the class is characterized by similar partition coefficients and, in consequence, similar environmental properties. Finally the data was fitted into a simple multimedia model involving the partitioning map. In addition, we found that the changes in the partition coefficients upon the replacement of chlorine with bromine were constant: 0.11, 0.31, and −0.21 per bromine atom for log KOW, log KOA, and log KAW, respectively. On the basis of this observation, a method for rapid estimation of changes in the partition coefficient upon chlorine−bromine substitution was proposed