Role of hydrogen bonding in the oxidation potential of enols

Three stable β,β‐dimesityl enols with heteroaromatic rings in the α‐position were synthesized to study the effect of OH···N hydrogen bonding on the oxidation potentials of enols. In contrast to its solid‐state structure, enol E1 exists predominantly as intramolecularly hydrogen‐bonded species in sol...

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Bibliographic Details
Published inJournal of physical organic chemistry Vol. 16; no. 7; pp. 373 - 379
Main Authors Lal, Mukul, Langels, Anja, Deiseroth, Hans-Jörg, Schlirf, Jens, Schmittel, Michael
Format Journal Article
LanguageEnglish
Published Chichester, UK John Wiley & Sons, Ltd 01.07.2003
Subjects
enols
hydrogen bonding
oxidation
redox potential
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Summary:Three stable β,β‐dimesityl enols with heteroaromatic rings in the α‐position were synthesized to study the effect of OH···N hydrogen bonding on the oxidation potentials of enols. In contrast to its solid‐state structure, enol E1 exists predominantly as intramolecularly hydrogen‐bonded species in solution. For enol E2 an intermolecular hydrogen bond and for E3 a partial proton transfer were established based on NMR, dilution experiments, solvent dependence and UV–visible spectroscopic studies. Cyclic voltammetric investigations revealed that OH···N hydrogen bonding may shift the oxidation potentials of enols by up to 510 mV cathodically. Copyright © 2003 John Wiley & Sons, Ltd.
Bibliography:ArticleID:POC650
istex:E08B9B33A62D00AC4EBC2F772D9A3AB64ACCCA6F
Deutsche Forschungsgemeinschaft
Fonds der Chemischen Industrie
ark:/67375/WNG-6CPW6DCW-L
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.650