Jump to main content
Jump to site search

Issue 21, 2012
Previous Article Next Article

Modulation of the antioxidant activity of phenols by non-covalent interactions

Author affiliations

Abstract

Non-covalent (H-bonding) interactions, either intramolecular or with the surrounding medium, have a major influence on the activity of natural and synthetic phenolic antioxidants, due to the modulation of their reactivity with radical species, such as peroxyl radicals. Different cases can be distinguished. (i) Intra- or inter-molecular H-bonding involving the reactive –OH moiety will depress the antioxidant activity if the –OH acts as H-bond donor, while the opposite will generally occur if it acts as H-bond acceptor. (ii) Remote intra- and inter-molecular H-bonding, involving a distant –OH group (in polyphenols) or a ring substituent, may increase or decrease the reactivity of an antioxidant toward free radicals, depending on whether the stabilization produced by the H-bond increases or decreases along the reaction coordinate, on proceeding from reactants to the transition state. In this Perspective, the role of non-covalent interactions in the complex chemistry of natural polyphenolic antioxidants is discussed with the aid of literature data on simplified model compounds, aiming at the composition of a clear picture that might guide future research.

Graphical abstract: Modulation of the antioxidant activity of phenols by non-covalent interactions

Back to tab navigation
Please wait while Download options loads

Publication details

The article was received on 23 Jan 2012, accepted on 19 Mar 2012 and first published on 19 Mar 2012


Article type: Perspective
DOI: 10.1039/C2OB25174D
Citation: Org. Biomol. Chem., 2012,10, 4147-4158
  •   Request permissions

    Modulation of the antioxidant activity of phenols by non-covalent interactions

    R. Amorati and L. Valgimigli, Org. Biomol. Chem., 2012, 10, 4147
    DOI: 10.1039/C2OB25174D

Search articles by author