Driving force and nucleophilicity in S(N)2 displacements.
The free energies of activation for reaction of six anionic nucleophiles with methyl iodide in dimethylformamide correlate linearly with the overall heats of reaction in the gas phase. The result indicates that nucleophilicity in this S(N)2 displacement reaction is dominated by electron affinity and bond-strength effects.
Streitwieser
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Department of Chemistry, University of California, Berkeley, CA 94720.