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Hydroperoxyl Radicals (HOO . ): Vitamin E Regeneration and H‐Bond Effects on the Hydrogen Atom Transfer
Author(s) -
Cedrowski Jakub,
Litwinienko Grzegorz,
Baschieri Andrea,
Amorati Riccardo
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.201603722
Subject(s) - hydroperoxyl , radical , hydrogen atom , chemistry , atom (system on chip) , photochemistry , solvent , hydrogen bond , molecule , organic chemistry , alkyl , computer science , embedded system
Hydroperoxyl (HOO . ) and alkylperoxyl (ROO . ) radicals show a different behavior in H‐atom‐transfer processes. Both radicals react with an analogue of α‐tocopherol (TOH), but HOO . , unlike ROO . , is able to regenerate TOH by a fast H‐atom transfer: TO . +HOO . →TOH+O 2 . The kinetic solvent effect on the H‐atom transfer from TOH to HOO . is much stronger than that observed for ROO . because noncovalent interactions with polar solvents (Solv⋅⋅⋅HOO . ) destabilize the transition state.