R. Clair, T. McMahon
Mar 1, 1979
Citations
0
Influential Citations
11
Citations
Journal
Canadian Journal of Chemistry
Abstract
Reactions of trifluoromethoxide ion, CF3O−, with carboxylic acids have been examined. Facile fluoride transfer is observed to occur to the acids and a subsequent fluoride transfer equilibrium established in mixtures of carboxylic acids. From the equilibrium constant obtained for fluoride transfer acetic acid and propionic acid are found to have near identical fluoride binding energies. Further reaction between the acid solvated fluoride ions and the carboxylic acids is observed to occur resulting in HF displacement and formation of bicarboxylate anions. In mixtures of acetic and propionic acids acetate and propionate anion transfer equilibria are again established. An analysis of the energetics for these processes reveals that propionic acid binds the carboxylate anions more strongly than acetic acid by 0.1 to 0.2 kcal/mol.