Competition between proton transfer and elimination in the reactions of strong bases with fluoroethanes in the gas phase. Influence of base strength on reactivity. [NH/sub 2//sup -/, OH/sup -/, CH/sub 3/O/sup -/, CH/sub 3/CH/sub 2/O/sup -/, (CH/sub 3/)/sub 2/ CHO/sup -/, (CH/sub 3/)/sub 3/ CO/sup -/, F/sup -/, and CN/sup -/]

Journal Article · Wed Mar 03 00:00:00 EST 1976 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00421a018· OSTI ID:7353049

Sullivan, S A; Beauchamp, J L

Fluoroethanes react with strong bases in the gas phase by proton transfer, elimination of HF, and production of F/sup -/. Ion cyclotron resonance spectroscopy has been used to examine the relative importance of these processes for a series of bases of varying strength, including NH/sub 2//sup -/, OH/sup -/, CH/sub 3/O/sup -/, CH/sub 3/CH/sub 2/O/sup -/, (CH/sub 3/)/sub 2/CHO/sup -/, (CH/sub 3/)/sub 3/CO/sup -/, F/sup -/, and CN/sup -/. 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 F/sup -/ to the fluoroethanes, fluoroethylenes, and HF 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. (auth)

• Research Organization: California Inst. of Tech., Pasadena, CA
• OSTI ID: 7353049
• Journal Information: J. Am. Chem. Soc.; (United States), Vol. 98:5
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
AMINES
CHEMICAL REACTION KINETICS
BASES
CYANIDES
FLUORIDES
FLUORINATED ALIPHATIC HYDROCARBONS
HYDROXIDES
BINDING ENERGY
ENTHALPY
FORMATION HEAT
GAS ANALYSIS
ION CYCLOTRON RESONANCE SPECTROSCOPY
ENERGY
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROGEN COMPOUNDS
ION SPECTROSCOPY
KINETICS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXYGEN COMPOUNDS
PHYSICAL PROPERTIES
REACTION HEAT
REACTION KINETICS
SPECTROSCOPY
THERMODYNAMIC PROPERTIES
400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)