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Concerted Proton–Electron Transfer in Pyridylphenols: The Importance of the Hydrogen Bond
Author(s) -
Markle Todd F.,
Mayer James M.
Publication year - 2008
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/anie.200702486
Subject(s) - pyridine , chemistry , phenol , proton , electron transfer , hydrogen bond , methylene , electron , transfer (computing) , hydrogen , group (periodic table) , photochemistry , computational chemistry , medicinal chemistry , molecule , organic chemistry , physics , nuclear physics , computer science , parallel computing
Slowed down by a break up : One‐electron oxidation of intramolecularly hydrogen‐bonded phenol–pyridine compounds 1 and 2 involves proton transfer coupled with electron transfer (see scheme; B=base). At the same driving force, 2 reacts substantially slower than 1 . The methylene group between the phenol and pyridine groups in 2 breaks the conjugation between the rings, which has a marked effect on the hydrogen bond and is likely the origin of the difference in rate constants.