Ferulic Acid as a Spin Trap: A Computational Study of Hydroxyl Radical Stabilization
Abstract
Hydroxyl radicals (•OH) are highly reactive species that contribute to oxidative stress and biomolecular damage in biological systems. Antioxidants such as ferulic acid (FA), a naturally occurring phenolic compound found in plant-based foods, may reduce this damage by stabilizing transient radicals through spin-adduct formation. However, the relative thermodynamic stability of possible FA–OH spin adducts has not been systematically evaluated using high-level quantum chemical methods. This study addresses the question of which carbon site on FA most favorably stabilizes hydroxyl radical addition, with the hypothesis that differences in electronic structure control radical selectivity. Hydroxyl radical addition at three carbon sites (C7, C8, and C9) on the FA framework was investigated using Hartree–Fock and Density Functional Theory methods. Geometry optimizations and harmonic vibrational analyses were performed with correlation-consistent and augmented basis sets. Electronic energies were extrapolated to the complete basis set limit using two independent two-point schemes, and zero-point energy corrections were included to obtain accurate stabilization energies. Across all computational approaches, C8 addition was consistently the most thermodynamically favorable. The stability ordering (C8 > C7 > C9) persists after vibrational corrections, supporting the hypothesis that electronic effects dominate radical selectivity. These findings identify C8 as the preferred spin-adduct formation site and provide molecular-level insight into how phenolic antioxidants stabilize reactive oxygen species, contributing to a broader understanding of oxidative stress mitigation.
Start Time
15-4-2026 1:30 PM
End Time
15-4-2026 4:30 PM
Room Number
Culp Ballroom 316
Presentation Type
Poster
Presentation Subtype
Posters - Competitive
Presentation Category
Science, Technology, and Engineering
Student Type
Graduate and Professional Degree Students, Residents, Fellows
Faculty Mentor
Scott Kirkby
Ferulic Acid as a Spin Trap: A Computational Study of Hydroxyl Radical Stabilization
Culp Ballroom 316
Hydroxyl radicals (•OH) are highly reactive species that contribute to oxidative stress and biomolecular damage in biological systems. Antioxidants such as ferulic acid (FA), a naturally occurring phenolic compound found in plant-based foods, may reduce this damage by stabilizing transient radicals through spin-adduct formation. However, the relative thermodynamic stability of possible FA–OH spin adducts has not been systematically evaluated using high-level quantum chemical methods. This study addresses the question of which carbon site on FA most favorably stabilizes hydroxyl radical addition, with the hypothesis that differences in electronic structure control radical selectivity. Hydroxyl radical addition at three carbon sites (C7, C8, and C9) on the FA framework was investigated using Hartree–Fock and Density Functional Theory methods. Geometry optimizations and harmonic vibrational analyses were performed with correlation-consistent and augmented basis sets. Electronic energies were extrapolated to the complete basis set limit using two independent two-point schemes, and zero-point energy corrections were included to obtain accurate stabilization energies. Across all computational approaches, C8 addition was consistently the most thermodynamically favorable. The stability ordering (C8 > C7 > C9) persists after vibrational corrections, supporting the hypothesis that electronic effects dominate radical selectivity. These findings identify C8 as the preferred spin-adduct formation site and provide molecular-level insight into how phenolic antioxidants stabilize reactive oxygen species, contributing to a broader understanding of oxidative stress mitigation.
