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Molecules 2013, 18(10), 11705-11711; doi:10.3390/molecules181011705
Article

Modes of Neighbouring Group Participation by the Methyl Selenyl Substituent in β-Methylselenylmethyl-substituted 1-Phenylethyl Carbenium Ions

 and *
School of Chemistry and BIO-21 Institute, University of Melbourne, Parkville 3010, Victoria, Australia
* Author to whom correspondence should be addressed.
Received: 29 July 2013 / Revised: 7 September 2013 / Accepted: 9 September 2013 / Published: 25 September 2013
(This article belongs to the Special Issue Selenium and Tellurium Chemistry)
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Abstract

Selenium substituents which are disposed β to an electron deficient centre, such as a carbocation p-orbital, or the π* orbital of an electron deficient p-system, interact in a stabilising way by a combination of C-Se hyperconjugation (σSe-Cπ* interaction), and a through-space homoconjugative nSe–π* interaction. The relative importance of these two modes of interaction is dependant on the electron demand of the cation, with hyperconjugation predominating for low electron demand systems, and the nSe–π* interaction predominating for high electron demand cations.
Keywords: hyperconjugation; stereoelectronic effects; selenium interactions hyperconjugation; stereoelectronic effects; selenium interactions
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Harris, B.L.; White, J.M. Modes of Neighbouring Group Participation by the Methyl Selenyl Substituent in β-Methylselenylmethyl-substituted 1-Phenylethyl Carbenium Ions. Molecules 2013, 18, 11705-11711.

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