Work

Typical Electron-Withdrawing Groups Are ortho, meta-Directors Rather than meta-Directors in Electrophilic Aromatic Substitution

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Electron-withdrawing groups are traditionally considered meta -directing in aromatic substitution reactions. However, when the pre-existing substituent is a π-acceptor, both experiment and calculation indicate that substantial amounts of ortho as well as meta substitution occur, with very little para reactivity. A simple perturbative MO argument rationalizes this finding. It is therefore suggested that these substituents are best understood as ortho, meta -directors, with a preference for meta, just as electron-donating groups are considered ortho, para -directors, with a preference for para .

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c00426

Author: Paul R. Rablen

Institution: Swarthmore College

Language: English

Topic: Chemical Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Swarthmore College