Radical-scavenging activity characterization of a series of synthetic 3-phenylcoumarins

• Published in: Computational and theoretical chemistry 2021-08, Vol.1202, p.113300, Article 113300
• Main Authors: Karadjova, Veronika, Vakarelska-Popovska, Maria, Velkov, Zhivko
• Format: Article
• Language: English
• Subjects: 3-phenylcoumarins; DFT-calculations; Mechanisms of O[sbnd]H bond dissociations; Radical-scavenging activity
• ISSN: 2210-271X
• DOI: 10.1016/j.comptc.2021.113300

Investigated processes. [Display omitted] •Synthetic phenylcoumarinswith assessed radical-scavenging activity are in focus.•Enthalpy changes of OH bond dissociations by different mechanisms are quantified.•Obtained values are compared to known phenolic acids, flavones and coumarins.•Measured radical-scavenging activities relate well with the calculated ETE values. A series of synthetic hydroxyl derivatives of 3-phenylcoumarin with already assessed radical-scavenging activity were modeled and treated with quantum-chemistry methods in order to get insight into the structural and energy changes occurring during dissociation of OH bonds by different mechanisms. The enthalpy changes of each step were calculated and the role of the OH-group positions in the molecules, as well as the influence of the second hydroxyl group on the reactivity were evaluated. The geometry of each intermediate structure was optimized using B3LYP/DFT functional and the standard 6-311++G(d,p) orbital basis set. Solvent effects were accounted for using the SCRF method, via the polarized continuum method.