Title of article
A pragmatic procedure for predicting regioselectivity in nucleophilic substitution of aromatic fluorides
Author/Authors
Liljenberg، نويسنده , , Magnus and Brinck، نويسنده , , Tore and Herschend، نويسنده , , Bjِrn and Rein، نويسنده , , Tobias and Rockwell، نويسنده , , Glen and Svensson، نويسنده , , Mats، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2011
Pages
4
From page
3150
To page
3153
Abstract
The scope and limitations of a method for predicting the regioisomer distribution in kinetically controlled nucleophilic substitution reactions of aromatic fluorides have been investigated. This method is based on calculating the relative stabilities of the isomeric σ-complex intermediates using DFT. A wide set of substrates and anionic nucleophiles have been investigated. Predictions from this method can be used quantitatively—these agree to an average accuracy of ±0.5 kcal/mol with experimental observations in eleven of the twelve investigated reactions.
Keywords
nucleophilic substitution , DFT , ?-Complex , computational , regioselectivity
Journal title
Tetrahedron Letters
Serial Year
2011
Journal title
Tetrahedron Letters
Record number
1878514
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