Ethene, fluoro-

Formula: C₂H₃F
Molecular weight: 46.0436
IUPAC Standard InChI: InChI=1S/C2H3F/c1-2-3/h2H,1H2
IUPAC Standard InChIKey: XUCNUKMRBVNAPB-UHFFFAOYSA-N
CAS Registry Number: 75-02-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: Ethylene, fluoro-; Fluoroethene; Fluoroethylene; Monofluoroethylene; Vinyl fluoride; C2H3F; 1-Fluoroethylene; FC 1141; Monofluoroethene
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- Gas Phase Kinetics Database
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-32.4	kcal/mol	Ccr	Kolesov and Papina, 1970
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-300.2 ± 0.4	kcal/mol	Ccr	Kolesov and Papina, 1970

Reaction thermochemistry data

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Data compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

C₂H₂F^- + = Ethene, fluoro-

By formula: C₂H₂F^- + H⁺ = C₂H₃F

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	386.7 ± 4.1	kcal/mol	G+TS	Rabasco and Kass, 1992	gas phase; Comparable to PhF. Vinyl anion structure proved, rxn with D2O -> more stable HC≡CH..F-; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	379.0 ± 4.0	kcal/mol	IMRB	Rabasco and Kass, 1992	gas phase; Comparable to PhF. Vinyl anion structure proved, rxn with D2O -> more stable HC≡CH..F-; B

+ Ethene, fluoro- = ( • )

By formula: F^- + C₂H₃F = (F^- • C₂H₃F)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	15.6 ± 4.0	kcal/mol	IMRB	Sullivan and Beauchamp, 1976	gas phase; B

Ethene, fluoro- + =

By formula: C₂H₃F + HF = C₂H₄F₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-12.	kcal/mol	Eqk	Moore, 1971	gas phase; ALS

Gas phase ion energetics data

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Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₂H₃F⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	10.36 ± 0.01	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	174.	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	167.3	kcal/mol	N/A	Hunter and Lias, 1998	HL

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.36 ± 0.02	PE	Bieri, Niessen, et al., 1981	LLK
10.3	PE	Dannacher, Schmelzer, et al., 1979	LLK
10.36	PE	Sell, Mintz, et al., 1978	LLK
10.363 ± 0.015	PI	Williamson and Beauchamp, 1976	LLK
10.37	PE	Reinke, Baumgartel, et al., 1974	LLK
10.35 ± 0.01	PI	Reinke, Kraessig, et al., 1973	LLK
10.37	PE	Lake and Thompson, 1970	RDSH
10.37 ± 0.02	PI	Momigny, 1963	RDSH
10.37	PI	Bralsford, Harris, et al., 1960	RDSH
10.63 ± 0.02	PE	Bieri, Niessen, et al., 1981	Vertical value; LLK
10.56 ± 0.02	PE	Sell and Kuppermann, 1979	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CF⁺	14.5 ± 0.1	CH₃	PE	Dannacher, Schmelzer, et al., 1979	LLK
CF⁺	15.43	?	EI	Lifshitz and Long, 1963	RDSH
C₂HF⁺	13.7 ± 0.1	H₂	PE	Dannacher, Schmelzer, et al., 1979	LLK
C₂HF⁺	13.72	H₂	PI	Reinke, Baumgartel, et al., 1974	LLK
C₂HF⁺	13.72 ± 0.02	H₂	PI	Reinke, Kraessig, et al., 1973	LLK
C₂HF⁺	14.04	H₂	EI	Lifshitz and Long, 1963	RDSH
C₂H₂⁺	13.30	HF	PE	Dannacher, Schmelzer, et al., 1979	LLK
C₂H₂⁺	13.51	HF	PI	Reinke, Baumgartel, et al., 1974	LLK
C₂H₂⁺	13.51 ± 0.02	HF	PI	Reinke, Kraessig, et al., 1973	LLK
C₂H₂⁺	13.7 ± 0.1	HF	EI	Lifshitz and Long, 1963	RDSH
C₂H₂F⁺	13.55	H	PE	Dannacher, Schmelzer, et al., 1979	LLK
C₂H₂F⁺	13.56	H	PI	Reinke, Baumgartel, et al., 1974	LLK
C₂H₂F⁺	13.56 ± 0.04	H	PI	Reinke, Kraessig, et al., 1973	LLK
C₂H₂F⁺	14.02	H	EI	Lifshitz and Long, 1963	RDSH
C₂H₃⁺	13.9 ± 0.1	F	PE	Dannacher, Schmelzer, et al., 1979	LLK
C₂H₃⁺	13.84	F	PI	Reinke, Baumgartel, et al., 1974	LLK
C₂H₃⁺	13.84 ± 0.04	F	PI	Reinke, Kraessig, et al., 1973	LLK
C₂H₃⁺	14.4 ± 0.1	F	EI	Lifshitz and Long, 1963	RDSH

De-protonation reactions

C₂H₂F^- + = Ethene, fluoro-

By formula: C₂H₂F^- + H⁺ = C₂H₃F

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	386.7 ± 4.1	kcal/mol	G+TS	Rabasco and Kass, 1992	gas phase; Comparable to PhF. Vinyl anion structure proved, rxn with D2O -> more stable HC≡CH..F-; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	379.0 ± 4.0	kcal/mol	IMRB	Rabasco and Kass, 1992	gas phase; Comparable to PhF. Vinyl anion structure proved, rxn with D2O -> more stable HC≡CH..F-; B

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	OV-101	230.	Zenkevich, 2005	25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; T_start: 50. C; T_end: 250. C

References

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Kolesov and Papina, 1970
Kolesov, V.P.; Papina, T.S., Standard enthalpy of formation of vinyl fluoride, Russ. J. Phys. Chem. (Engl. Transl.), 1970, 44, 611-613. [all data]

Rabasco and Kass, 1992
Rabasco, J.J.; Kass, S.R., Reactions of Strong Bases with Vinyl Fluoride Formation and Characterization of 1-Fluorovinyl Anion and the Fluoride-Acetylene Hydrogen-Bond, J. Am. Soc. Mass Spectrom., 1992, 3, 2, 91, https://doi.org/10.1016/1044-0305(92)87041-V . [all data]

Sullivan and Beauchamp, 1976
Sullivan, S.A.; Beauchamp, J.L., Competition between proton transfer and elimination in the reactions of strong bases with fluoroethanes in the gas phase. Influence of base strength on reactivity, J. Am. Chem. Soc., 1976, 98, 1160. [all data]

Moore, 1971
Moore, L.O., Kinetics and thermodynamic data for the hydrogen fluoride addition to vinyl fluoride, Can. J. Chem., 1971, 49, 2471-2475. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Bieri, Niessen, et al., 1981
Bieri, G.; Niessen, W.V.; Asbrink, L.; Svensson, A., The He(II) photoelectron spectra of the fluorosubstituted ethylenes and their analysis by the green's function method, Chem. Phys., 1981, 60, 61. [all data]

Dannacher, Schmelzer, et al., 1979
Dannacher, J.; Schmelzer, A.; Stadelmann, J.-P.; Vogt, J., A photoelectron-photoion coincidence study of vinylfluoride, Int. J. Mass Spectrom. Ion Phys., 1979, 31, 175. [all data]

Sell, Mintz, et al., 1978
Sell, J.A.; Mintz, D.M.; Kupperman, A., Photoelectron angular distributions of carbon-carbon π electrons in ethylene, benzene, and their fluorinated derivatives, Chem. Phys. Lett., 1978, 58, 601. [all data]

Williamson and Beauchamp, 1976
Williamson, A.D.; Beauchamp, J.L., Ion molecule reactions in vinyl fluoride by photoionization. Effects of vibrational excitation on major reaction pathways, J. Chem. Phys., 1976, 65, 3196. [all data]

Reinke, Baumgartel, et al., 1974
Reinke, D.; Baumgartel, H.; Cvitas, T.; Klasinc, L.; Gusten, H., Vergleich der Photoelektronenspektren und Photoionenspektren von Vinylfluorid, Ber. Bunsen-Ges. Phys. Chem., 1974, 78, 1145. [all data]

Reinke, Kraessig, et al., 1973
Reinke, D.; Kraessig, R.; Baumgartel, H., Photoreactions of small organic molecules, Z. Naturforsch. A:, 1973, 28, 1021. [all data]

Lake and Thompson, 1970
Lake, R.F.; Thompson, H., Photoelectron spectra of halogenated ethylenes, Proc. Roy. Soc. (London), 1970, A315, 323. [all data]

Momigny, 1963
Momigny, J., Ionization potentials and the structures of the photo-ionization yield curves of ethylene and its halogeno derivatives, Nature, 1963, 199, 1179. [all data]

Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C., The effect of fluorine on the electronic spectra and ionization potentials of molecules, Proc. Roy. Soc. (London), 1960, A258, 459. [all data]

Sell and Kuppermann, 1979
Sell, J.A.; Kuppermann, A., Variable angle photoelectron spectroscopy of the fluoroethylenes, J. Chem. Phys., 1979, 71, 4703. [all data]

Lifshitz and Long, 1963
Lifshitz, C.; Long, F.A., Appearance potentials and mass spectra of fluorinated ethylenes. I. Decomposition mechanisms and their energetics, J. Phys. Chem., 1963, 67, 2463. [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
IE (evaluated)	Recommended ionization energy
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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