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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 (closed 20110630).ORCID iD: 0000-0003-2673-075X
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2011 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 52, 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 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.

Place, publisher, year, edition, pages
Elsevier, 2011. Vol. 52, 3150-3153 p.
Keyword [en]
Nucleophilic substitution; Regioselectivity; Computational; sigma-Complex; DFT
National Category
Physical Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-204496DOI: 10.1016/j.tetlet.2011.04.032ISI: 000292350800023ScopusID: 2-s2.0-79956042668OAI: oai:DiVA.org:kth-204496DiVA: diva2:1084963
Note

Artikeln ingår som ett delarbete i en doktorsavhandling. QC 20170411

Available from: 2017-03-27 Created: 2017-03-27 Last updated: 2017-04-11Bibliographically approved

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