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A Remarkable, Stable Radical–Molecule Complex: HO 2 ⋅CF 3 C(O)OH
Author(s) -
Francisco Joseph S.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20001215)39:24<4570::aid-anie4570>3.0.co;2-i
Subject(s) - hydroperoxyl , hydrogen bond , trifluoroacetic acid , chemistry , molecule , covalent bond , photochemistry , density functional theory , computational chemistry , radical , organic chemistry
Unusually strong hydrogen bonding results in the formation of a stable complex between trifluoroacetic acid (TFA) and the hydroperoxyl radical (see picture). Density functional calculations predict that HO 2 ⋅CF 3 C(O)OH, held together by cyclic hydrogen bonding, has a binding energy of 15.1 kcal mol −1 , comparable in magnitude to weak covalent bonding. This may have implications for the atmospheric chemistry of TFA, which is a product of the atmospheric oxidation of alternative chlorofluorocarbons such as HCFC‐123.