The O–H and S–H homolytic bond dissociation enthalpies of a set of disubstituted phenols and thiophenols (NH2, OH, CH3, Cl, CF3, and NO2) have been computed by a density functional theory procedure with the 6-311++G(d,p) basis set. A very good agreement between our results and available experimental ones is observed. The effect of substituents on structure, charges and BDEs are investigated and their correlation with Hammett parameters is studied.
Daniel J. V. A. dos Santos1, Ana S. Newton1, Raul Bernardino2, Rita C. Guedes1
1 iMed.UL/CECF, Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto,
1649-003 Lisbon, Portugal
2 Instituto Politécnico de Leiria, Escola Superior Tecnologia do Mar, Santuário N.a Sra. dos Remédios, Apartado 126, 2524–909 Peniche, Portugal