Computation of relative bond dissociation enthalpies (DeltaBDE) of phenolic antioxidants from quantum topological molecular similarity (QTMS).
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 (DeltaBDEs) 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 DeltaBDEs 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 q(2) = 0.85 for the bond dissociation enthalpies of this phenolic antioxidant data set.
Singh
Nakul
N
School of Chemistry, The University of Manchester, Manchester M60 1QD, UK.
Loader
Robert J
RJ
O'Malley
Patrick J
PJ
Popelier
Paul L A
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