Jump to main content
Jump to site search

Issue 5, 2013
Previous Article Next Article

Gas-phase dissociative electron attachment to flavonoids and possible similarities to their metabolic pathways

Author affiliations

Abstract

The gas-phase empty-level structures and formation of anion states via resonance attachment of low-energy electrons to the flavonoids naringenin (III), quercetin (IV) and myricetin (V) and the smaller reference molecules chromone (I) and flavone (II) are investigated experimentally for the first time. Dissociative electron attachment spectroscopy (DEAS) is used to measure the fragment anion currents generated through dissociative decay channels of the molecular anions of compounds I–V, detected with a mass filter as a function of the incident electron energy in the 0–14 eV energy range. Due to the insufficient volatility of flavonoids III–V, the energies of vertical electron attachment associated with temporary occupation of the lower-lying virtual orbitals are measured with electron transmission spectroscopy (ETS) only in the smaller reference molecules I and II. The experimental findings are interpreted with the support of appropriate density functional theory calculations with the B3LYP functional. The experimental vertical electron attachment energies measured in the ET spectra of I and II are compared with the orbital energies of the neutral molecules scaled using an empirically calibrated linear equation. The vertical and adiabatic electron affinities are evaluated at the B3LYP/6-31+G(d) level as the anion/neutral total energy difference. The latter theoretical method is also used for evaluation of the most stable conformers of the neutral molecules, O–H bond dissociation energies and thermodynamic energy thresholds for production of the anion fragments observed in the DEA spectra. A possible role played by loss of an H2 molecule from the parent molecular anion in vivo in the mitochondrial respiratory chain is briefly discussed.

Graphical abstract: Gas-phase dissociative electron attachment to flavonoids and possible similarities to their metabolic pathways

Back to tab navigation

Publication details

The article was received on 25 Sep 2012, accepted on 22 Nov 2012 and first published on 23 Nov 2012


Article type: Paper
DOI: 10.1039/C2CP43379F
Citation: Phys. Chem. Chem. Phys., 2013,15, 1588-1600
  •   Request permissions

    Gas-phase dissociative electron attachment to flavonoids and possible similarities to their metabolic pathways

    A. Modelli and S. A. Pshenichnyuk, Phys. Chem. Chem. Phys., 2013, 15, 1588
    DOI: 10.1039/C2CP43379F

Search articles by author

Spotlight

Advertisements