Abstract
A recently proposed method called quantitative topological molecular similarity (QTMS) generated a model for the computation of the relative substituent effects on the bond dissociation enthalpies (ΔBDEs) for a set of 39 phenols. The data set includes a diverse set of substituents with monosubstituted and poly-substituted derivatives that exhibit different electronic and steric effects. Many share common structural features with already well-established antioxidants. QTMS reveals the active region of the substituted phenols and identifies the electronic descriptors that best explain the range of ΔBDEs observed. For substituents in the 4-X position (para) we find that our model requires a correction for radical stabilization enthalpy (RSE). Application of the QTMS methodology yields an unrivalled QSAR with r 2 = 0.98 and q2 = 0.85 for the bond dissociation enthalpies of this phenolic antioxidant data set. © 2006 American Chemical Society.
Original language | English |
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Pages (from-to) | 6498-6503 |
Number of pages | 5 |
Journal | Journal of Physical Chemistry A |
Volume | 110 |
Issue number | 20 |
DOIs | |
Publication status | Published - 25 May 2006 |