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

Lage, Mateus R.; Morbec, Juliana M.; Santos, Marcelo H.; Carneiro, José Walkimar de M.; Costa, Luciano T.

Authors

Mateus R. Lage

Marcelo H. Santos

José Walkimar de M. Carneiro

Luciano T. Costa



Abstract

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 ?B97x-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.)

Acceptance Date Jan 23, 2017
Publication Date Mar 30, 2017
Journal Journal of Molecular Modeling
Print ISSN 1610-2940
Publisher Springer Verlag
DOI https://doi.org/10.1007/s00894-017-3251-x
Keywords Epiclusianone, Tautomerism, DFT, QTAIM
Publisher URL https://link.springer.com/article/10.1007%2Fs00894-017-3251-x#aboutcontent

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