Abstract:
Nucleophilic reactions which are studied in proton donating solvents are complicated by the proton transfer from the solvent (commonly alcohol) to the nucleophilic reagent Y- with the subsequent establishment of the equilibrium
This effect was recognised and qualitatively detected by Cox (J 1918, 66; 1922, 493) in his study of the relative reactivities of various alkyl halides with sodium 1- and 2- napthoxides in alcohol and by Haywood (J 1922, 121, 1904) in similar studies with sodium benzyl oxide.
Quantitative studies of the magnitude and importance of this effect on reaction rates have only been investigated recently, Baker and Neale (J 1954, 3225.) on the study of attack of aryl-oxide ions on benzyl nitrate in ethanol and England (Chem and Ind . 1954, 1145) with the attack of sodium phenoxide on organic halides in methanol.
