SCHEDULED MAINTENANCE
Mechanism of aromatic nucleophilic substitution in aprotic solvents
Abstract
The effect of various hydrogen-bond acceptors on the reactions of 1-chloro- and 1-fluoro-2,4-dinitrobenzenes with morpholine in benzene at 30°C has been investigated. The reaction of the chloro substrate is not base-catalysed and the additives produced no acceleration in the concentrations employed. The reaction of the fluoro substrate is base-catalysed. The addition of hydrogen-bond acceptors frequently leads to accelerations which vary linearly with the concentration of the acceptor. An approximately linear relationship exists between the logarithm of the slope of these correlations and the hydrogen-bonding parameter pkHB. These effects are interpreted as electrophilic catalysis, by the heteroconjugates of the acceptors with the conjugate acid of morpholine, of the ratedetermining decomposition of the intermediate in these reactions.
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