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

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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

Harris BL, White JM. Modes of Neighbouring Group Participation by the Methyl Selenyl Substituent in β-Methylselenylmethyl-substituted 1-Phenylethyl Carbenium Ions. Molecules. 2013; 18(10):11705-11711.

Chicago/Turabian Style

Harris, Benjamin L.; White, Jonathan M. 2013. "Modes of Neighbouring Group Participation by the Methyl Selenyl Substituent in β-Methylselenylmethyl-substituted 1-Phenylethyl Carbenium Ions." Molecules 18, no. 10: 11705-11711.

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