A pragmatic procedure for predicting regioselectivity in nucleophilic substitution of aromatic fluorides

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...

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Bibliographic Details
Published in:Tetrahedron letters 2011-06, Vol.52 (24), p.3150-3153
Main Authors: Liljenberg, Magnus, Brinck, Tore, Herschend, Björn, Rein, Tobias, Rockwell, Glen, Svensson, Mats
Format: Article
Language:English
Subjects:
Chemistry
Computational
DFT
Exact sciences and technology
Fluorides
Kinetics and mechanisms
Mathematical analysis
Nucleophiles
Nucleophilic substitution
Organic chemistry
Reactivity and mechanisms
Regioselectivity
Stability
Substitution reactions
Tetrahedrons
σ-Complex
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Summary: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.
ISSN:0040-4039
1359-8562
1873-3581
DOI:10.1016/j.tetlet.2011.04.032