The Cation-π Interaction in Small-Molecule Catalysis

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2016 Jun 23

PMID 27329991

Citations 47

Authors

C Rose Kennedy

Song Lin

Eric N Jacobsen

Affiliations

Soon will be listed here.

Abstract

Catalysis by small molecules (≤1000 Da, 10(-9) m) that are capable of binding and activating substrates through attractive, noncovalent interactions has emerged as an important approach in organic and organometallic chemistry. While the canonical noncovalent interactions, including hydrogen bonding, ion pairing, and π stacking, have become mainstays of catalyst design, the cation-π interaction has been comparatively underutilized in this context since its discovery in the 1980s. However, like a hydrogen bond, the cation-π interaction exhibits a typical binding affinity of several kcal mol(-1) with substantial directionality. These properties render it attractive as a design element for the development of small-molecule catalysts, and in recent years, the catalysis community has begun to take advantage of these features, drawing inspiration from pioneering research in molecular recognition and structural biology. This Review surveys the burgeoning application of the cation-π interaction in catalysis.

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