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DFT insights into the structure, reactivity and radical scavenging activity of cycloartocarpesin
Author(s) -
Tamafo Fouegue Aymard Didier,
Tedongmo Hilaire,
Abdoul Ntieche Rahman,
Ghogomu Julius Numbonui
Publication year - 2021
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.4245
Subject(s) - chemistry , reactivity (psychology) , radical , antioxidant , density functional theory , ionization energy , fukui function , computational chemistry , hydrogen bond , photochemistry , ionization , proton , electron affinity (data page) , electron transfer , electronic structure , medicinal chemistry , molecule , organic chemistry , catalysis , medicine , ion , physics , alternative medicine , electrophile , pathology , quantum mechanics
Abstract Daily increase in the number of patients suffering from illnesses due to reactive species has induced the permanent discovery and study of antioxidant compounds. The structure, reactivity, and antioxidant activity (AOA) of a phenolic compound named cycloartocarpesin (CAP), evaluated at DFT/B3LYP/6‐31 + G(d,p) level, is reported herein in the gas, pentyl ethanoate, and water phases. Bader topological analysis revealed that two of the three O‐H groups of CAP are involved in hydrogen bonds while the average local ionization energy (ALIE) and appropriate Fukui functions showed that electrons in the near vicinity of C 7 , C 10 , and C 12 are the least tightly held and can easily be attacked by radicals. Analysis of the transition state of the reaction between CAP and HOO • radical shows that the proton coupled electron transfer process is not favored. Moreover, analyses of electronic spectra calculated at TD‐DFT/B3LYP/6‐31 + G(d,p) has interestingly demonstrate the ability of CAP to filtrate UVA, UVB, and UVC, thus exhibiting a photo‐protective activity.