Premium
Structure and reactivity of baicalein radical cation
Author(s) -
Marković Zoran S.,
Marković Svetlana,
Dimitrić Marković Jasmina M.,
Milenković Dejan
Publication year - 2011
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.23175
Subject(s) - baicalein , chemistry , density functional theory , radical , radical ion , proton , delocalized electron , reactivity (psychology) , electron transfer , molecule , computational chemistry , quantum chemical , spin density , photochemistry , organic chemistry , ion , pathology , quantum mechanics , medicine , genetics , physics , alternative medicine , biology , condensed matter physics
Neutral baicalein, corresponding radical cation, and three possible radicals obtained by proton removal from the radical cation were investigated using density functional theory. The structure and UV spectrum of baicalein were very well reproduced by the B3LYP/6‐311+G(2df,p) level of theory. The results showed that the loss of an electron from baicalein molecule induced the transfer of H4 to O5. The reasons for this rearrangement were pointed out. It was found that delocalization of spin density is most pronounced in the thermodynamically most stable C6OH radical. It was supposed that this radical plays a significant role in the antioxidant activity of baicalein within the single‐electron transfer‐proton transfer mechanism. © 2011 Wiley Periodicals, Inc. Int J Quantum Chem, 2011