Next Article in Journal
A Commonly Used Chinese Herbal Formula, Shu-Jing-Hwo-Shiee-Tang, Potentiates Anticoagulant Activity of Warfarin in a Rabbit Model
Previous Article in Journal
Characterization of Amide Bond Conformers for a Novel Heterocyclic Template of N-acylhydrazone Derivatives
Previous Article in Special Issue
Synthesis and Biological Activity of 6-Selenocaffeine: Potential Modulator of Chemotherapeutic Drugs in Breast Cancer Cells
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)
View Full-Text   |   Download PDF [461 KB, uploaded 18 June 2014]   |   Browse Figures
SciFeed

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 (CC BY 3.0).

Supplementary material

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert