Fluoroethanes react with strong bases in the gas phase by proton transfer, elimination of HF, and production of F-. Ion cyclotron resonance spectroscopy has been used to examine the relative importance of these processes for a series of bases of varying strength, including NH2-, OH-, CHsO-, C H~C H Z O -, (CH3)2CHO-, (CH3)3CO-, F-, and CN-. Reactant base strength is the principal factor determining product distributions. With decreasing base strength, the amount of proton transfer decreases relative to elimination. Observed proton transfer reactions establish limits for the acidities of the fluoroethanes. In addition, binding energies of Fto the fluoroethanes, fluoroethylenes, and H F have been determined. With these thermochemical data, a satisfactory explanation of the effect of base strength on reactivity is provided by the application of straightforward concepts of unimolecular reaction kinetics.
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