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A pragmatic procedure for predicting regioselectivity in nucleophilic substitution of aromatic fluorides
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.ORCID iD: 0000-0003-2673-075X
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2011 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1873-3581, Vol. 52, no 24, 3150-3153 p.Article in journal (Refereed) Published
Abstract [en]

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 sigma-complex intermediates using OFT. 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.

Place, publisher, year, edition, pages
2011. Vol. 52, no 24, 3150-3153 p.
Keyword [en]
Nucleophilic substitution, Regioselectivity, Computational, sigma-Complex, DFT
National Category
Physical Chemistry
URN: urn:nbn:se:kth:diva-36885DOI: 10.1016/j.tetlet.2011.04.032ISI: 000292350800023ScopusID: 2-s2.0-79956042668OAI: diva2:431505
QC 20110720Available from: 2011-07-20 Created: 2011-07-18 Last updated: 2011-07-20Bibliographically approved

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