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Effect of Molecular Interactions on Electron‐Transfer and Antioxidant Activity of Bis(alkanol)selenides: A Radiation Chemical Study
Author(s) -
Kumar Pavitra V.,
Singh Beena G.,
Phadnis Prasad P.,
Jain Vimal K.,
Priyadarsini K. Indira
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601918
Subject(s) - antioxidant , electron transfer , chemistry , radiation , photochemistry , physics , biochemistry , nuclear physics
Understanding electron‐transfer processes is crucial for developing organoselenium compounds as antioxidants and anti‐inflammatory agents. To find new redox‐active selenium antioxidants, we have investigated one‐electron‐transfer reactions between hydroxyl ( . OH) radical and three bis(alkanol)selenides (SeROH) of varying alkyl chain length, using nanosecond pulse radiolysis. . OH radical reacts with SeROH to form radical adduct, which is converted primarily into a dimer radical cation (>Se∴Se<) + and α‐{bis(hydroxyl alkyl)}‐selenomethine radical along with a minor quantity of an intramolecularly stabilized radical cation. Some of these radicals have been subsequently converted to their corresponding selenoxide, and formaldehyde. Estimated yield of these products showed alkyl chain length dependency and correlated well with their antioxidant ability. Quantum chemical calculations suggested that compounds that formed more stable (>Se∴Se<) + , produced higher selenoxide and lower formaldehyde. Comparing these results with those for sulfur analogues confirmed for the first time the distinctive role of selenium in making such compounds better antioxidants.