Quantifying the Role of Anion−π Interactions in Anion−π Catalysis
Organic Letters2014Vol. 16(12), pp. 3268–3271
Citations Over TimeTop 10% of 2014 papers
Abstract
Matile et al. introduced the concept of anion-π catalysis [Angew. Chem., Int. Ed. 2013, 52, 9940; J. Am. Chem. Soc. 2014, 136, 2101], reporting naphthalene diimide (NDI)-based organocatalysts for the Kemp elimination reaction. We report computational analyses of the operative noncovalent interactions, revealing that anion-π interactions actually increase the activation barriers for some of these catalyzed reactions. We propose new catalysts that are predicted to achieve significant lowering of the activation energy through anion-π interactions.
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