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 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	-136.	kJ/mol	Ccr	Kolesov and Papina, 1970
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-1256. ± 2.	kJ/mol	Ccr	Kolesov and Papina, 1970

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity	Value	Units	Method	Reference	Comment
T_boil	201.	K	N/A	PCR Inc., 1990	BS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
16.6	186.	A	Stephenson and Malanowski, 1987	Based on data from 124. to 201. K. See also Stull, 1947.; AC

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
123.8 to 201.0	3.46439	593.551	-30.039	Stull, 1947	Coefficents calculated by NIST from author's data.

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)	729.	kJ/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	700.1	kJ/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°	1618. ± 17.	kJ/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°	1586. ± 17.	kJ/mol	IMRB	Rabasco and Kass, 1992	gas phase; Comparable to PhF. Vinyl anion structure proved, rxn with D2O -> more stable HC≡CH..F-; B

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]

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

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]

Notes

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Symbols used in this document:

AE	Appearance energy
IE (evaluated)	Recommended ionization energy
T_boil	Boiling point
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
Δ_vapH	Enthalpy of vaporization

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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