A Lewis Acidity Scale in Relation to Rate Constants of Lewis Acid Catalyzed Organic Reactions
Authors:
- 13 September 2011
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2011 (30) , 5962-5966
Abstract
The quantification of Lewis acidity is accomplished by a deuterated quinolizidine probe utilizing 2H NMR spectroscopy. The chemical shifts of the 2H 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 2H 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.Keywords
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