Abstract
The environmental fate of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans (PCDD/Fs) has become a major issue in recent decades. Quantitative structure-property relationship (QSPR) modeling is a powerful approach for predicting the properties of environmental organic pollutants from their structure descriptors. In this study, QSPR models were established for estimating water solubility (-log SW) and n-octanol/water partition coefficient (log KOW) of PCDD/Fs. Quantum chemical descriptors computed with density functional theory at the B3LYP/6-31G(d) level and partial least squares (PLS) analysis with an optimizing procedure were used to generate QSPR models for -log SW and log KOW of PCDD/Fs. Optimized models with high correlation coefficients (R2 > 0.983) were obtained for estimating -log SW and log KOW of PCDD/Fs. Both the internal cross validation test (Q 2cum > 0.978) and external validation test (R 2 > 0.965) results showed that the obtained models had high-precision and good prediction capability. The -log SW} and log KOW values predicted by the obtained models are very close to those observed. The PLS analysis indicated that PCDD/Fs with larger electronic spatial extent (Re), lower molecular total energy (ET), and smaller energy gap between the lowest unoccupied and the highest occupied molecular orbitals (ELUMO-EHOMO) tend to be less soluble in water but more lipophilic.
Original language | English (US) |
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Pages (from-to) | 9-22 |
Number of pages | 14 |
Journal | Journal of Theoretical and Computational Chemistry |
Volume | 9 |
Issue number | SUPPL. 1 |
DOIs | |
State | Published - 2010 |
All Science Journal Classification (ASJC) codes
- Computer Science Applications
- Physical and Theoretical Chemistry
- Computational Theory and Mathematics
Keywords
- N-octanol/water partition coefficient.
- PCDD/Fs
- QSPR
- Water solubility