Related Experiment Video
Updated: Jan 26, 2026
Fabricating Complex Culture Substrates Using Robotic Microcontact Printing R- µCP and Sequential Nucleophilic Substitution
Published on: October 31, 2014
Concerted Nucleophilic Aromatic Substitution Reactions
Simon Rohrbach1, Andrew J Smith1, Jia Hao Pang2
1Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.
A new class of nucleophilic aromatic substitution reactions, known as concerted nucleophilic aromatic substitution (cSN Ar), has been discovered. These reactions do not require the strong activating groups typical of traditional SN Ar mechanisms.
Area of Science:
- Organic Chemistry
- Reaction Mechanisms
Background:
- Nucleophilic aromatic substitution (SN Ar) traditionally proceeds via a two-step mechanism.
- This mechanism typically requires strong electron-withdrawing groups to activate the aromatic ring.
Purpose of the Study:
- To identify and characterize a new class of SN Ar reactions.
- To explore reaction pathways that deviate from the classical SN Ar mechanism.
Main Methods:
- Experimental chemistry techniques.
- Computational chemistry modeling.
Main Results:
- Identification of a growing class of concerted nucleophilic aromatic substitution (cSN Ar) reactions.
- Demonstration that cSN Ar pathways do not necessitate strong electron-withdrawing substituents for activation.
Conclusions:
- Concerted SN Ar mechanisms represent a significant departure from classical SN Ar pathways.
- The discovery expands the scope and applicability of nucleophilic aromatic substitution reactions in organic synthesis.
Related Concept Videos
01:30Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
02:34Nucleophilic Substitution Reactions
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
01:17Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
01:16Electrophilic Aromatic Substitution: Overview