DFT INSIGHT INTO THE UV-VIS SPECTRA AND RADICAL SCAVENGING ACTIVITY OF AURANTIO-OBTUSIN
Publication in refereed journal

香港中文大學研究人員

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其它資訊
摘要Aurantio-obtusin (2,6,8-trihydroxy-1,7-dimethoxy-3-methyl anthraquinone), an anthraquinone derivative isolated from the seeds of Cassia tora L., has been studied by DFT calculations at the B3LYP/6-311+g(2df, p)//B3LYP/6-31G(d, p) level in vacuum and in methanol polarized continuum model (PCM). Eight conformers have been located by conformational search and optimization. Our results indicate that the titled compound has planar structures, and five intramolecular hydrogen bonds are found in the lowest-energy structure, including three OH center dot center dot center dot O and two CH center dot center dot center dot O hydrogen bonds. The electronic spectra in methanol have been determined by the time-dependent density functional theory (TD-DFT) approach, showing that the first singlet exited state of the title compound arises from pi -> pi* electron transition. The antioxidant activity of aurantio-obtusin is evaluated by means of calculating O-H bond dissociated enthalpy (BDE) and the adiabatic ionization energy (IE). The calculated BDE and IE values of aurantio-obtusin are 341.8 and 732.3 kJ mol(-1), respectively, lower than the corresponding values of phenol (348.4 and 801.7 kJ mol(-1)) and purpurin (360.4 and 747.8 kJ mol(-1)), suggesting that aurantio-obtusin is a better antioxidant.
著者Xu SC, Ren Y, Wan L, Li WK, Wong NB, Zhang JX, Liao Q, Ji L
期刊名稱Journal of Theoretical and Computational Chemistry
出版年份2013
月份6
日期1
卷號12
期次4
出版社WORLD SCIENTIFIC PUBL CO PTE LTD
國際標準期刊號0219-6336
電子國際標準期刊號1793-6888
語言英式英語
關鍵詞antioxidant activity; Aurantio-obtusin; DFT calculations; time-dependent DFT; UV-Vis spectrum
Web of Science 學科類別Chemistry; Chemistry, Multidisciplinary; CHEMISTRY, MULTIDISCIPLINARY

上次更新時間 2020-27-10 於 00:40