Abstract
The rates of reaction of methyl iodide with chloride ion in some protic-dipolar aprotic solvent mixtures have been measured. The rate-retarding effect of protic solvents at M concentration in dimethylacetamide is in the order p-NO2C6H4OH > C6H5OH > C6H5SH > C6H5CO2H ≈ CH3OH > C6H5NH2 >H2O ≈ D2O. Protic solvents slow the reaction by a general rather than a specific hydrogen bonding interaction with the anion. Both the dipolar aprotic solvent and the protic solvent, as well as the anion, accept hydrogen bonds, and this influences the interaction between protic solvent and anion.
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