Acta Chimica Slovaca (ACS) publishes papers on fundamental and applied aspects of chemistry, biochemistry, chemical technology, chemical engineering and process control, biotechnology and food technology. Welcome are also topics which include chemical aspects of materials, physical chemistry and chemical physics, analytical chemistry, macromolecular chemistry and biomedical engineering.

Influence of catecholic ring torsion on hydroxyflavones

Martin Michalík *, Monika Biela, Denisa Cagardová, Vladimír Lukeš

Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia

E-mail: *

Abstract: Systematic quantum chemical investigation of quercetin and selected eight mono- and bi-hydroxyflavonols is presented. Structural analysis based on the Density Functional Theory showed that the energetically preferred conformation of flavonols substituted at the C5 and C3 atoms by a hydroxyl group is stabilised via intramolecular hydrogen bonds occurring between the (C4)O···HO(3 or 5) atomic pairs. Depending on the hydroxyl group positions, energetically preferred torsional orientation of the phenyl ring with respect to the planar benzo-g-pyrone moiety changed from 0 to 180 degrees. Gas-phase electron transitions were investigated using the time-dependent DFT treatment. The dependence of maximal wavelengths on the torsional deformation of the phenyl ring is of a similar shape, i.e. minima observed for the perpendicular orientation and maxima for the planar one. Shape and energies of the Highest Occupied (HOMO) and Lowest Unoccupied (LUMO) Molecular Orbitals were compared. The obtained theoretical results were compared with available experimental data.

Keywords: BDE, hydroxyflavones, torsion

Full paper in Portable Document Format: acs_0357.pdf

Acta Chimica Slovaca, Vol. 13, No. 1, 2020, pp. 49—55, DOI: 10.2478/acs-2020-0008