Natural polyprenylated benzophenone: keto-enol tautomerism from density functional calculations and the AIM theory

• Autor(a) principal: Santos, Marcelo H.
• Data de Publicação: 2017
• Outros Autores: Lage, Mateus R., Morbec, Juliana M., Carneiro, José Walkimar de M., Costa, Luciano T.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: LOCUS Repositório Institucional da UFV
• Texto Completo: http://dx.doi.org/10.1007/s00894-017-3251-x; http://www.locus.ufv.br/handle/123456789/19663
• topic: Epiclusianone; Tautomerism; DFT; QTAIM

The quantum theory of atoms in molecules (QTAIM) and density functional theory (DFT) calculations were employed to investigate the structure and tautomeric equilibrium of epiclusianone, a polyisoprenylated benzophenone with interesting biological activities. Two different exchange-correlation functionals were employed, namely ωB97x-D and M06-2x, including implicit solvent models (benzene and DMSO). Our results for the thermodynamic properties show that the isomer in which the H atom is bonded to the oxygen away from the benzene ring is the most stable tautomer form of the epiclusianone, thus confirming previous charge density analysis from X-ray diffraction data (Martins et al. J Braz Chem Soc 18(8):1515–1523, 2007).