A meta effect in nonphotochemical processes: the homolytic chemistry of m-methoxyphenol

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DOIResolve DOI: http://doi.org/10.1021/jo702520r
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TypeArticle
Journal titleJournal of Organic Chemistry
ISSN0022-3263
Volume73
Issue6
Pages24082411; # of pages: 4
SubjectElectron-donating (ED); Electron-withdrawing (EW); Homolytic chemistry; M-methoxy group; Excited states; Free radicals; Photoexcitation; Phenols; 3 methoxyphenol; mequinol; phenol derivative; unclassified drug; article; chemistry; hydrogen bond; Anisoles; Photochemistry; Thermodynamics
Abstract(Chemical Equation Presented) The m-methoxy group is normally electron-withdrawing (EW), σm = +0.12, σm+ = +0.05. The strong EW activity of a phenoxyl radical's O • atom causes the m-methoxy group to become electron-donating (ED), σm+ = -0.14. In valence bond terms, this can be ascribed to the nonclassical resonance structures 1c-e. Although it has long been known that m-methoxy is ED in photoexcited states, it has now been found to be ED for homolytic O-H bond breaking in ground-state 3-methoxyphenol. © 2008 American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; National Institute for Nanotechnology; NRC Steacie Institute for Molecular Sciences
Peer reviewedYes
NPARC number21276541
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Record identifier15bede1d-4240-4da5-a6aa-f8fcdc77063e
Record created2015-10-13
Record modified2016-05-09
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