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

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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)
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.
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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