| Download | - View final version: A meta effect in nonphotochemical processes: the homolytic chemistry of m-methoxyphenol (PDF, 242 KiB)
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| DOI | Resolve DOI: https://doi.org/10.1021/jo702520r |
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| Author | Search for: Foti, M. C.; Search for: Daquino, C.; Search for: DiLabio, G. A.1; Search for: Ingold, K. U.2 |
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| Affiliation | - National Research Council of Canada. National Institute for Nanotechnology
- National Research Council of Canada. NRC Steacie Institute for Molecular Sciences
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| Format | Text, Article |
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| Subject | electron-donating (ED); electron-withdrawing (EW); homolytic chemistry; m-methoxy group; excited states; free radicals; photoexcitation; phenols; 3 methoxyphenol; mequinol; phenol derivative; unclassified drug; chemistry; hydrogen bond; anisoles; photochemistry; thermodynamics |
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| 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. |
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| Publication date | 2008-02-23 |
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| Publisher | American Chemical Society |
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| In | |
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| Note | Correction published in volume 73, issue 18, page 7440, July 29th 2008. DOI: 10.1021/jo8014374 |
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| Language | English |
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| Peer reviewed | Yes |
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| NPARC number | 21276541 |
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| Export citation | Export as RIS |
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| Report a correction | Report a correction (opens in a new tab) |
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| Record identifier | 15bede1d-4240-4da5-a6aa-f8fcdc77063e |
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| Record created | 2015-10-13 |
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| Record modified | 2020-05-15 |
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