Cover Feature: Flipping the Metalation of 4‐Dimethylaminopyridine: Steric Repulsion versus London Dispersion Attraction (Chem. Eur. J. 6/2025)
Year: 2025
Type: article
Abstract: Dispersion interactions serve as a driving force for ortho-lithiation: A significantly large and bulky substituent, rich in C−H bonds, attached to the pyridine nitrogen of 4-dimethylaminopyridine, strongly attracts the organolithium reagent through dispersion forces. This interaction is visualized as a black hole drawing the organolithium particle toward it. In contrast, simpler bulky substituents repel incoming organometallic reagents, diverting them to position 3 instead. This repulsion is metaphorically represented as a star emitting a particle outward. More information can be found in the Research Article by A. S. Antonov and co-workers (DOI: 10.1002/chem.202403422).
Source: Chemistry - A European Journal
Institutions: St Petersburg University, University of Regensburg
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4406866019