Molecular Diversity

, Volume 15, Issue 1, pp 173–188

Estimating persistence of brominated and chlorinated organic pollutants in air, water, soil, and sediments with the QSPR-based classification scheme

Full-Length Paper

DOI: 10.1007/s11030-010-9250-9

Cite this article as:
Puzyn, T., Haranczyk, M., Suzuki, N. et al. Mol Divers (2011) 15: 173. doi:10.1007/s11030-010-9250-9

Abstract

We have estimated degradation half-lives of both brominated and chlorinated dibenzo-p-dioxins (PBDDs and PCDDs), furans (PBDFs and PCDFs), biphenyls (PBBs and PCBs), naphthalenes (PBNs and PCNs), diphenyl ethers (PBDEs and PCDEs) as well as selected unsubstituted polycyclic aromatic hydrocarbons (PAHs) in air, surface water, surface soil, and sediments (in total of 1,431 compounds in four compartments). Next, we compared the persistence between chloro- (relatively well-studied) and bromo- (less studied) analogs. The predictions have been performed based on the quantitative structure-property relationship (QSPR) scheme with use of k-nearest neighbors (kNN) classifier and the semi-quantitative system of persistence classes. The classification models utilized principal components derived from the principal component analysis of a set of 24 constitutional and quantum mechanical descriptors as input variables. Accuracies of classification (based on an external validation) were 86, 85, 87, and 75% for air, surface water, surface soil, and sediments, respectively. The persistence of all chlorinated species increased with increasing halogenation degree. In the case of brominated organic pollutants (Br-OPs), the trend was the same for air and sediments. However, we noticed that the opposite trend for persistence in surface water and soil. The results suggest that, due to high photoreactivity of C–Br chemical bonds, photolytic processes occurring in surface water and soil are able to play significant role in transforming and removing Br-OPs from these compartments. This contribution is the first attempt of classifying together Br-OPs and Cl-OPs according to their persistence, in particular, environmental compartments.

Keywords

Brominated organic pollutants Half-lives QSPR kNN Class of persistence 

Supplementary material

11030_2010_9250_MOESM1_ESM.xls (2.5 mb)
ESM 1 (XLS 2,543 kb)

Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  1. 1.Faculty of Chemistry, Laboratory of Environmental ChemometricsUniversity of GdańskGdańskPoland
  2. 2.Computational Research DivisionLawrence Berkeley National LaboratoryBerkeleyUSA
  3. 3.National Institute for Environmental Studies, Research Center for Environmental Risk, Exposure Assessment Research SectionTsukubaJapan

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