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dc.creatorRamalho, Teodorico C.-
dc.creatorPereira, Douglas H.-
dc.date.accessioned2020-05-18T05:13:57Z-
dc.date.available2020-05-18T05:13:57Z-
dc.date.issued2009-10-
dc.identifier.citationRAMALHO, T. C.; PEREIRA, D. H. Understanding the substituent effect on the acidity of alcohols and para-substituted phenols. Molecular Simulation, [S.l.], v. 35, n. 15, p. 1269-1278, Oct. 2009. DOI: 10.1080/08927020903015387.pt_BR
dc.identifier.urihttps://www.tandfonline.com/doi/abs/10.1080/08927020903015387pt_BR
dc.identifier.urihttp://repositorio.ufla.br/jspui/handle/1/41010-
dc.description.abstractWe carried out Hartree–Fock (HF) and density functional theory calculations on the conjugated bases of phenols and alcohols for 23 compounds and analysed their acid–base behaviour using molecular orbital (MO) energies and their dependence on solvent effects. Despite the well-known correlation between highest-occupied MO (HOMO) energies and proton affinity (PA), we observed that HOMO energies are inadequate to describe the acid–base behaviour of these compounds. Therefore, we established a criterion to identify the best frontier MO for describing PA values and also to understand why the HOMO approach fails. The MO that fits our criterion provided very good correlations with PA values, much better than those obtained by the HOMO energies. Since the frontier MOs are those which drive the acid–base reactions in each compound, they were called frontier effective-for-reaction MOs, or FERMOs. By using the FERMO concept, the reactions that are HOMO driven, and those that are not, can be better explained, independent of the calculation method used, since both HF and Kohn-Sham methodologies lead to the same FERMO.pt_BR
dc.languageen_USpt_BR
dc.publisherTaylor & Francispt_BR
dc.rightsrestrictAccesspt_BR
dc.sourceMolecular Simulationpt_BR
dc.subjectAcidity of alcoholspt_BR
dc.subjectHOMO-LUMOpt_BR
dc.subjectFERMOpt_BR
dc.subjectMolecular orbitalpt_BR
dc.titleUnderstanding the substituent effect on the acidity of alcohols and para-substituted phenolspt_BR
dc.typeArtigopt_BR
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