Posts Tagged ‘Meisenheimer’

Concerted vs stepwise (Meisenheimer) mechanisms for aromatic nucleophilic substitution.

Monday, March 25th, 2013

My two previous explorations of aromatic substitutions have involved an electrophile (NO+ or Li+). Time now to look at a nucleophile, representing nucleophilic aromatic substitution. The mechanism of this is thought to pass through an intermediate analogous to the Wheland for an electrophile, this time known as the Meisenheimer complex[cite]10.1002/jlac.19023230205[/cite]. I ask the same question as before; are there any circumstances under which the mechanism could instead be concerted, by-passing this intermediate?