The effect of substituents on the electrochemical oxidation potentials of 1,1,2,2-tetraphenylcyclopropane and 1,1,3,3-tetraphenylpropenyl radical

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DOIResolve DOI: http://doi.org/10.1139/v86-017
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TypeArticle
Journal titleCanadian Journal of Chemistry
ISSN0008-4042
Volume64
Issue1
Pages100103; # of pages: 4
AbstractThe effects of multiple substitution by methoxy and cyano in the 4-position(s) of 1,1,2,2-tetraphenylcyclopropane (1) and 1,1,3,3-tetraphenylpropenyl radical (2•) on the oxidation potentials have been measured. The results indicate that the oxidation process for the cyclopropanes (1a–m) is irreversible. Nevertheless, the substituent effect on the potential is essentially additive and correlates reasonably well with ??+. A slow electron transfer process (an overall conversion of 1 to 2+), with a transition state resembling the ring-opened radical cation, is consistent with these observations. The oxidation of the radical 2• is quasi-reversible in dichloromethane. In this case also, the substituent effect on the oxidation potential is additive and correlates with ??+. Any deviation from planarity of 2• is not sufficient to prevent substituents from exerting normal (additive) behaviour.
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LanguageEnglish
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Identifier10000872
NPARC number12328322
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Record identifier5568fa38-edd2-470e-b734-adafe47c8b50
Record created2009-09-10
Record modified2016-05-09
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