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Liquid‐phase theoretical antioxidant activity trend of some cinnamic acid antioxidants
Author(s) -
Lithoxoidou Alexandra T.,
Bakalbassis Evangelos G.
Publication year - 2004
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-004-0981-9
Subject(s) - heptane , chemistry , antioxidant , polarizable continuum model , solvent , hydrogen bond , solvent effects , cinnamic acid , acetonitrile , organic chemistry , density functional theory , bond dissociation energy , dissociation (chemistry) , computational chemistry , molecule
Abstract The trend in antioxidant activity of four cinnamic acid antioxidants, derived on the basis of their liquid‐phase phenolic O H bond dissociation enthalpies, is determined theoretically, with the aid of the polarizable continuum model at the density functional theory level. Three solvents, differing in their hydrogen‐bonding ability and polarity— n ‐heptane, acetonitrile, and ethanol—were used to model different environmental situations. The trends in solution‐phase antioxidant activity appeared different in each solvent; still, the theoretical antioxidant activity trend derived in n ‐heptane was in excellent agreement with the experimental one in the lipid systems and the gas‐phase system. Different ortho substituents show notably different solvent effects. These results could lead to the determination of reliable antioxidant activity trends in real‐solution environments of interest in food or biological science frameworks.