Electrophilicity of quinones and its relationship with hydride affinity

In this Letter we show that the electrophilicity index assesses well the hydride affinity ( HA) order of quinones established for a limited number of cases experimentally observed. Further comparisons with predicted HA values for a larger data base suggest that both the electrophilicity index and HA are tightly related quantities. Furthermore, electrophilic activation/deactivation patterns induced by electron-withdrawing and electron-donating groups may be consistently accounted for by the model. These results open the possibility of predicting HA for quinones not evaluated experimentally up to date. (C) 2009 Elsevier B.V. All rights reserved.