Quantitative structureproperty relationships on dissolvability of pcdd/fs using quantum chemical descriptors and partial least squares

Gui Ning Lu, Xue Qin Tao, Z. H.I. Dang, Weilin Huang, Zhong Li

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

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 languageEnglish (US)
Pages (from-to)9-22
Number of pages14
JournalJournal of Theoretical and Computational Chemistry
Volume9
Issue numberSUPPL. 1
DOIs
StatePublished - 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

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