Jump to main content
Jump to site search

Issue 7, 2009
Previous Article Next Article

Steric effects of nucleophile-radical coupling reaction. Determination of rate constants for the reaction of aryl radicals with 2-naphthoxide anion

Author affiliations

Abstract

The absolute rate constants for the reaction of different aryl radicals with 2-naphthoxide anion were determined using an indirect method, a competition of the coupling reaction with the H-atom abstraction. We here show that the radical-ambident nucleophile reactions are sensitive to steric hindrance. A lower reactivity is found for 2-anisyl radical with respect to 4-anisyl and for 2-methoxy-1-naphthyl radical with respect to 1-naphthyl (k2b < k2a and k2d < k2c). The ortho substitution to the radical centre decreases the rate constant. The reactivity is in agreement with energy barriers determined by theoretical calculations.

Graphical abstract: Steric effects of nucleophile-radical coupling reaction. Determination of rate constants for the reaction of aryl radicals with 2-naphthoxide anion

Back to tab navigation

Supplementary files

Article information


Submitted
19 Nov 2008
Accepted
11 Feb 2009
First published
23 Mar 2009

New J. Chem., 2009,33, 1523-1528
Article type
Paper

Steric effects of nucleophile-radical coupling reaction. Determination of rate constants for the reaction of aryl radicals with 2-naphthoxide anion

T. C. Tempesti, A. B. Pierini and M. T. Baumgartner, New J. Chem., 2009, 33, 1523
DOI: 10.1039/B820374A

Social activity

Search articles by author

Spotlight

Advertisements