Antioxidant and spectral properties of chalcones and analogous aurones: Theoretical insights

作者：Xue, Yunsheng^*; Liu, Yunping; Zhang, Ling; Wang, Han; Luo, Qingquan; Chen, Ran; Liu, Yin; Li, Ya

来源：International Journal of Quantum Chemistry, 2019, 119(3): e25808.

DOI：10.1002/qua.25808

• aurones
• chalcones
• density functional theory
• mechanism
• radical scavenging activity

Density functional theory (DFT) and time-dependent DFT (TD-DFT) have been employed to elucidate the radical scavenging capacity and the UV-Vis spectral property of several chalcones and analogous aurones. Three main antioxidant mechanisms, hydrogen atom transfer (HAT), electron transfer followed by proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) were investigated. The results indicate that all the studied compounds adopt a fully planar conformation in their neutral, radical, cationic as well as anionic forms. 2 '-OH plays important role in the stabilization of phenolic radicals due to the formation of intramolecular hydrogen bonds (IHBs). Introduction of electron-donating substituent on B-ring is helpful for improving the activity. For the considered compounds, HAT is proposed as the thermodynamically favored mechanism in gas phase and nonpolar environment, while SPLET is preferred in polar media. The results confirmed the crucial role of hydroxyl group on A-ring, especially on position 5 '/5, in terms of the radical scavenging ability. The absorption spectra of title compounds were successfully simulated and the lowest energy transitions predominantly correspond to the pi-pi* transitions from HOMO to LUMO with charge transfer (CT) character.

• 出版日期2019-2-5
• 单位徐州医科大学