π–π Catalysis in Carbon Flatland—Flipping [8]Annulene on Graphene

Asja A. Kroeger, Amir Karton

Research output: Contribution to journalArticle

Abstract

Noncovalent interactions are an integral part of the modern catalysis toolbox. Although stronger noncovalent interactions such as hydrogen bonding are commonly the main driving force of catalysis, π–π interactions typically provide smaller additional stabilizations, for example, to afford selectivity enhancements. Here, it is shown computationally that pristine graphene flakes may efficiently catalyze the skeletal inversions of various benzannulated cyclooctatetraene derivatives, providing an example of a catalytic process driven solely by π–π stacking interactions. Hereby, the catalytic effect results from disproportionate shape complementarity between catalyst and transition structure compared with catalyst and reactant. An energy decomposition analysis reveals electrostatic and, especially with increasing system size, to a larger extent, dispersion interactions as the origin of stabilization.

Original languageEnglish
Pages (from-to)3420-3426
Number of pages7
JournalChemistry - A European Journal
Volume27
Issue number10
DOIs
Publication statusPublished - 15 Feb 2021

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