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• W2314579439 endingPage "9898" @default.
• W2314579439 startingPage "9893" @default.
• W2314579439 abstract "The anodic oxidation of methyl 3-phenyl-2-dimethylsilylpropionate occurs at a potential almost 1 V positive of that required to oxidize other alpha-silyl esters. Semiempirical and ab initio calculations on the model compound 1-phenyl-2-trimethylsilylethane indicate that electron removal from these two compounds is highly stereoelectronically dependent. Both molecules exist almost exclusively in a conformation in which the phenyl group and silicon atom are anti and the side chain is perpendicular to the aromatic ring. This conformation has a higher energy HOMO orbital and lower computed ionization potential than the only other significantly populated conformation of 1-phenyl-2-trimethylsilylethane. Finally, the ab initio calculations show that in the cation radical of this model compound the ipso carbon of the aromatic ring and the side chain carbon bound to silicon draw significantly closer together than in the neutral species; an electrostatic potential map of the cation radical shows that the ipso carbon bears the highest degree of positive charge of any of the benzenoid carbons. We interpret these data, taken together, as an indication that this cation radical is stabilized by overlap of the rear lobe of the carbon-silicon bond with the p-orbital of the ipso carbon." @default.
• W2314579439 created "2016-06-24" @default.
• W2314579439 creator A5012260975 @default.
• W2314579439 creator A5086708138 @default.
• W2314579439 date "2003-11-21" @default.
• W2314579439 modified "2023-09-23" @default.
• W2314579439 title "Anodic Oxidation of Methyl α-Dimethylsilyldihydrocinnamate. A Novel Silicon γ<i>-</i>Aryl Effect" @default.
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• W2314579439 doi "https://doi.org/10.1021/jo030264e" @default.
• W2314579439 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/14682680" @default.
• W2314579439 hasPublicationYear "2003" @default.
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