A meta effect in nonphotochemical processes: the homolytic chemistry of m-methoxyphenol |
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Authors: | Foti Mario C Daquino Carmelo DiLabio Gino A Ingold K U |
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Institution: | Istituto di Chimica Biomolecolare del CNR, Via del Santuario 110, I-95028 Valverde (CT) Italy. mario.foti@icb.cnr.it |
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Abstract: | The m-methoxy group is normally electron-withdrawing (EW), sigma(m) = +0.12, sigma(m+) = +0.05. The strong EW activity of a phenoxyl radical's O* atom causes the m-methoxy group to become electron-donating (ED), sigma(m)(+) = -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. |
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