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A Lewis Acidity Scale in Relation to Rate Constants of Lewis Acid Catalyzed Organic Reactions

✍ Scribed by Gerhard Hilt; Florian Pünner; Juri Möbus; Vesal Naseri; Martin A. Bohn

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
248 KB
Volume
2011
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The quantification of Lewis acidity is accomplished by a deuterated quinolizidine probe utilizing ^2^H NMR spectroscopy. The chemical shifts of the ^2^H NMR signals for aluminum, boron, titanium, and zinc halides are reported. The rate constants for Lewis acid catalyzed reactions were determined by utilizing UV/Vis spectroscopy for Diels–Alder and Povarov reactions under pseudo‐first‐order conditions. The magnitude of the ^2^H NMR chemical shifts correlates with the rate constants of the organic transformations for many Lewis acids investigated in the same order, whereas some deviations are identified.

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