Ammonia, methylamine, dimethylamine, and trimethylamine react with methyl iodide in water at only about 4 times the rates in benzene because the corresponding transition states are either of the same free energy or of higher free energy in water as compared with benzene.
M. H. Abraham, J. Chem. Soc. D, 1970, 293 DOI: 10.1039/C29700000293
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