Enthalpies of Transfer of Transition States in the Menshutkin Reaction from a Polar Protic to a Dipolar Aprotic Solvent

Paul Habebfield, Allen Bloom, Richard Romm, Henry Ginsberg, Abraham Nudelman

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Abstract

The rates of the reaction of pyridine with six benzyl halides in methanol and dimethylformamide (DMF) were determined at 25.0 and 50.0°. The heats of solution of the reactants in these two solvents were determined at 25.0°. From these data the enthalpies of transfer of the transition states of these reactions from methanol to dimethylformamide were calculated. In all cases the lower activation enthalpy in the dipolar aprotic solvent was found to be caused entirely by greater solvation of the transition state in the dipolar aprotic solvent rather than by solvation effects on the reactants. Some effects upon this transition state of changes in the leaving group and in the substrate are discussed.

Original languageEnglish
Pages (from-to)1792-1795
Number of pages4
JournalJournal of Organic Chemistry
Volume36
Issue number13
DOIs
StatePublished - 1 Jul 1971
Externally publishedYes

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