Electronic eigenvalue (EEVA): a new QSAR/QSPR descriptor for electronic substituent effects based on molecular orbital energies. A QSAR approach to the Ah receptor binding affinity of polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs)

Chemosphere. 2000 Sep;41(6):843-8. doi: 10.1016/s0045-6535(99)00525-1.

Abstract

A new descriptor of molecular structure for use in the derivation of predictive QSAR and QSPR models, electronic eigenvalue (EEVA), is described. This is a modification of the recently proposed EVA approach, but is based on computationally-derived molecular orbital energies instead of vibrational frequencies. Like EVA, it is also invariant as to the alignment of the structures concerned. Its performance has been tested with respect to the Ah receptor binding of PCBs, PCDDs and PCDFs, and its predictive ability has been clearly demonstrated. In particular, it seems to be suitable for 'pure' electronic substituent effects. i.e., for cases in which both hydrophobic and steric factors are of minor importance.

MeSH terms

  • Algorithms*
  • Benzofurans / chemistry
  • Benzofurans / metabolism*
  • Models, Chemical
  • Polychlorinated Biphenyls / chemistry
  • Polychlorinated Biphenyls / metabolism*
  • Polychlorinated Dibenzodioxins / analogs & derivatives*
  • Polychlorinated Dibenzodioxins / chemistry
  • Polychlorinated Dibenzodioxins / metabolism
  • Receptors, Aryl Hydrocarbon / chemistry
  • Receptors, Aryl Hydrocarbon / metabolism*
  • Structure-Activity Relationship*

Substances

  • Benzofurans
  • Polychlorinated Dibenzodioxins
  • Receptors, Aryl Hydrocarbon
  • dibenzofuran
  • Polychlorinated Biphenyls