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 *
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)
Download PDF [461 KB, uploaded 18 June 2014]
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.

Export to BibTeX |
EndNote


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.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert