Ethene, chloro-

Formula: C₂H₃Cl
Molecular weight: 62.498
IUPAC Standard InChI: InChI=1S/C2H3Cl/c1-2-3/h2H,1H2
IUPAC Standard InChIKey: BZHJMEDXRYGGRV-UHFFFAOYSA-N
CAS Registry Number: 75-01-4
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, chloro-; Chloroethene; Chloroethylene; Monochloroethylene; Vinyl chloride; Vinyl chloride monomer; Vinyl C monomer; C2H3Cl; Ethylene monochloride; Monochloroethene; Chlorethene; Chlorethylene; Chlorure de vinyle; Cloruro di vinile; Rcra waste number U043; Trovidur; UN 1086; VC; VCM; Vinylchlorid; Vinyle(chlorure de); Winylu chlorek
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
Options:
- Switch to SI units

Data at NIST subscription sites:

NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes

Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	5.3 ± 0.7	kcal/mol	Review	Manion, 2002	weighted average of several measurements; DRB
Δ_fH°_gas	7.0	kcal/mol	Eqk	Levanova, Treger, et al., 1976	ALS
Δ_fH°_gas	5.0	kcal/mol	Eqk	Alfassi, Golden, et al., 1973	Heat of reaction not reported; ALS
Δ_fH°_gas	8.43 ± 0.33	kcal/mol	Cm	Lacher, Gottlieb, et al., 1962	Reanalyzed by Cox and Pilcher, 1970, Original value = 8.07 ± 0.28 kcal/mol; ALS
Δ_fH°_gas	9.10 ± 0.20	kcal/mol	Chyd	Lacher, Emery, et al., 1956	Reanalyzed by Cox and Pilcher, 1970, Original value = 8.9 ± 0.2 kcal/mol; At 298 K, see Lacher, Kianpour, et al., 1956; ALS

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes

Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	0.2 ± 0.76	kcal/mol	Review	Manion, 2002	derived from recommended Δ_fH_gas° and Δ_vapH°; DRB
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	28.20	cal/mol*K	N/A	Lebedev, Rabinovich, et al., 1967	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
21.38	298.15	Lebedev, Rabinovich, et al., 1967	T = 58 to 300 K.; DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes

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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

= Ethene, chloro- +

By formula: C₂H₄Cl₂ = C₂H₃Cl + HCl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	12.1 ± 1.0	kcal/mol	Cm	Buravtsev, Grigor'ev, et al., 1992	gas phase
Δ_rH°	19.6	kcal/mol	Eqk	Levanova, Bushneva, et al., 1979	liquid phase
Δ_rH°	16.3	kcal/mol	Eqk	Levanova, Bushneva, et al., 1979	gas phase
Δ_rH°	16.24	kcal/mol	Eqk	Ghosh and Guha, 1951	liquid phase

= Ethene, chloro- +

By formula: C₂H₄Cl₂ = C₂H₃Cl + HCl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	17.8	kcal/mol	Eqk	Levanova, Bushneva, et al., 1979	liquid phase
Δ_rH°	14.8	kcal/mol	Eqk	Levanova, Bushneva, et al., 1979	gas phase

2 + Ethene, chloro- = +

By formula: 2H₂ + C₂H₃Cl = C₂H₆ + HCl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-51.2 ± 0.2	kcal/mol	Chyd	Lacher, Emery, et al., 1956	gas phase; At 298 K, see Lacher, Kianpour, et al., 1956

= + Ethene, chloro-

By formula: C₂H₄BrCl = HBr + C₂H₃Cl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	19.9 ± 0.2	kcal/mol	Eqk	Busheva, Levanova, et al., 1980	gas phase; Dehydrohalogenation

+ Ethene, chloro- = +

By formula: H₂ + C₂H₃Cl = C₂H₄ + HCl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-18.39	kcal/mol	Chyd	Lacher, Kianpour, et al., 1956	gas phase; At 298 K

= Ethene, chloro-

By formula: C₂H₃Cl = C₂H₃Cl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-42.1 ± 3.7	kcal/mol	Cm	LaVilla and Goodman, 1989	gas phase; solvent: Heptane

Ethene, chloro- = +

By formula: C₂H₃Cl = C₂H₂ + HCl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	24.06 ± 0.28	kcal/mol	Cm	Lacher, Gottlieb, et al., 1962	gas phase

= Ethene, chloro- +

By formula: C₂H₃ClN₂ = C₂H₃Cl + N₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-46.9 ± 3.4	kcal/mol	Cm	Archer and Tyler, 1976	gas phase

Ethene, chloro- + =

By formula: C₂H₃Cl + HCl = C₂H₄Cl₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-22.15	kcal/mol	Eqk	Levanova, Treger, et al., 1976	gas phase

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes

Data evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C₂H₃Cl⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	9.99 ± 0.02	eV	N/A	N/A	L

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.98 ± 0.02	PI	Sheng, Qi, et al., 1995	LL
9.99 ± 0.02	PI	Reinke, Kraessig, et al., 1973	LLK
10.01	PE	Mines and Thompson, 1973	LLK
10.00	PE	Lake and Thompson, 1970	RDSH
10.00 ± 0.01	PI	Sood and Watanabe, 1966	RDSH
10.00 ± 0.01	S	Sood and Watanabe, 1966	RDSH
10.00 ± 0.02	PI	Momigny, 1963	RDSH
10.0 ± 0.01	PI	Watanabe, Nakayama, et al., 1962	RDSH
9.995	PI	Bralsford, Harris, et al., 1960	RDSH
10.00 ± 0.01	S	Walsh, 1945	RDSH
10.2	PE	Cambi, Ciullo, et al., 1983	Vertical value; LBLHLM
10.2	PE	Von Niessen, Asbrink, et al., 1982	Vertical value; LBLHLM
10.15	PE	Wittel and Bock, 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₂H₂⁺	12.5 ± 0.1	HCl	PI	Reinke, Kraessig, et al., 1973	LLK
C₂H₂⁺	13.8 ± 0.3	HCl	EI	Hughes, Tiernan, et al., 1969	RDSH
C₂H₂Cl⁺	14.90 ± 0.05	H	PI	Sheng, Qi, et al., 1995	LL
C₂H₃⁺	12.54 ± 0.02	Cl	PI	Sheng, Qi, et al., 1995	LL
C₂H₃⁺	12.48 ± 0.04	Cl	PI	Reinke, Kraessig, et al., 1973	LLK
C₂H₃⁺	12.56 ± 0.09	Cl	EI	Finney and Harrison, 1972	LLK
C₂H₃⁺	12.5	Cl	EI	Lossing, 1971	LLK
H⁺	18.63 ± 0.05	C₂H₂Cl	PI	Sheng, Qi, et al., 1995	LL

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

Manion, 2002
Manion, J.A., Evaluated Enthalpies of Formation of the Stable Closed Shell C1 and C2 Chlorinated Hydrocarbons, J. Phys. Chem. Ref. Data, 2002, 31, 1, 123-172, https://doi.org/10.1063/1.1420703 . [all data]

Levanova, Treger, et al., 1976
Levanova, S.V.; Treger, Yu.A.; Velichko, S.M.; Rozhnov, A.M., Equilibria in the reactions of vinyl chloride, Russ. J. Phys. Chem. (Engl. Transl.), 1976, 50, 1148. [all data]

Alfassi, Golden, et al., 1973
Alfassi, Z.B.; Golden, D.M.; Benson, S.W., The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the C_d-(H)(X) group, J. Chem. Thermodyn., 1973, 5, 411-420. [all data]

Lacher, Gottlieb, et al., 1962
Lacher, J.R.; Gottlieb, H.B.; Park, J.D., Reaction heats of organic compounds. Part 2.-Heat of addition of hydrogen chloride to acetylene, Trans. Faraday Soc., 1962, 58, 2348-2351. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Lacher, Emery, et al., 1956
Lacher, J.R.; Emery, E.; Bohmfalk, E.; Park, J.D., Reaction heats of organic compounds. IV. A high temperature calorimeter and the hydrogenation of methyl ethyl and vinyl chlorides, J. Phys. Chem., 1956, 60, 492-495. [all data]

Lacher, Kianpour, et al., 1956
Lacher, J.R.; Kianpour, A.; Oetting, F.; Park, J.D., Reaction calorimetry. The hydrogenation of organic fluorides and chlorides, Trans. Faraday Soc., 1956, 52, 1500-1508. [all data]

Lebedev, Rabinovich, et al., 1967
Lebedev, B.V.; Rabinovich, I.B.; Budarina, V.A., Heat capacity of vinyl chloride, polyvinylchloride and polyvinylidene chloride in the region of 60-300°K, Polymer Sci., 1967, USSR 9A, 545-552. [all data]

Buravtsev, Grigor'ev, et al., 1992
Buravtsev, N.N.; Grigor'ev, A.S.; Zaidman, O.A.; Kolbanovskii, Yu.A.; Markelov, M.YU.; Sadogurskii, M.N.; Treger, Yu.A., Dehydrochlorination of chloroalkanes under rigid homogeneous conditions. II. Effect of small additions of oxygen to the kinetics of high-temperature decomposition of 1,2-dichloroethane under adiabatic compression, Khim. Fiz., 1992, 11, 218-226. [all data]

Levanova, Bushneva, et al., 1979
Levanova, s.V.; Bushneva, I.I.; Rodova, R.M.; Rozhnov, A.M.; Treger, Yu.A.; Aprelkin, A.S., Thermodynamic stability of chloroethanes in dehydrochlorination reactions, J. Appl. Chem. USSR, 1979, 52, 1439-1442. [all data]

Ghosh and Guha, 1951
Ghosh, J.C.; Guha, S.R.D., Catalytic dehydrochlorination of ethylene dichloride, Petroleum (London), 1951, 14, 261-264. [all data]

Busheva, Levanova, et al., 1980
Busheva, L.I.; Levanova, S.V.; Rodova, R.M.; Rozhnov, A.M., Thermocatalytic reactions of 1,1-bromochloroethane, Russ. J. Phys. Chem. (Engl. Transl.), 1980, 54, 1403-1404. [all data]

LaVilla and Goodman, 1989
LaVilla, J.A.; Goodman, J.L., The 1,2-hydrogen-shift rearrangement in alkylchlorocarbenes, J. Am. Chem. Soc., 1989, 111, 6877-6878. [all data]

Archer and Tyler, 1976
Archer, W.H.; Tyler, B.J., Self-heating in the decomposition of 3-methyl-3-chlorodiazirine: Determination of reaction exothermicity and correction of Arrhenius parameters, J. Chem. Soc. Faraday Trans. 1, 1976, 72, 1448-1455. [all data]

Sheng, Qi, et al., 1995
Sheng, L.; Qi, F.; Tao, L.; Zhang, Y.; Yu, S.; Wong, C.-K.; Li, W.-K., Experimental and theoretical studies of the photoionization and dissociative photoionization of vinyl chloride, Int. J. Mass Spectrom. Ion Processes, 1995, 148, 179. [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]

Mines and Thompson, 1973
Mines, G.W.; Thompson, H.W., Photoelectron spectra of vinyl and allyl halides, Spectrochim. Acta Part A, 1973, 29, 1377. [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]

Sood and Watanabe, 1966
Sood, S.P.; Watanabe, K., Absorption and ionization coefficients of vinyl chloride, J. Chem. Phys., 1966, 45, 2913. [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]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]

Walsh, 1945
Walsh, A.D., The absorption spectra of the chloro ethylenes in the vacuum ultra-violet, J. Chem. Soc. Faraday Trans., 1945, 41, 35. [all data]

Cambi, Ciullo, et al., 1983
Cambi, R.; Ciullo, G.; Sgamellotti, A.; Tarantelli, F.; Fantoni, R.; Giardini-Guidoni, A.; McCarthy, I.E.; di Martino, V., An (e,2e) spectroscopic investigation and a Green's Function Study of the ionization of chloro- and bromoethylene, Chem. Phys. Lett., 1983, 101, 477. [all data]

Von Niessen, Asbrink, et al., 1982
Von Niessen, W.; Asbrink, L.; Bieri, G., 30.4 nm He(II) Photoelectron spectra of organic molecules. Part VI. Halogeno-compounds (C,H,X: X = Cl, Br, I), J. Electron Spectrosc. Relat. Phenom., 1982, 26, 173. [all data]

Wittel and Bock, 1974
Wittel, K.; Bock, H., Photoelektronenspekten und molekuleigenschaften. XXVII. Chlor- und bromathylene- beispiele fur anderungen in π- und σ-Systemen, Chem. Ber., 1974, 107, 317. [all data]

Hughes, Tiernan, et al., 1969
Hughes, B.M.; Tiernan, T.O.; Futrell, J.H., Ionic reactions in unsaturated compounds. IV. Vinyl chloride, J. Phys. Chem., 1969, 73, 829. [all data]

Finney and Harrison, 1972
Finney, C.D.; Harrison, A.G., A third-derivative method for determining electron-impact onset potentials, Int. J. Mass Spectrom. Ion Phys., 1972, 9, 221. [all data]

Lossing, 1971
Lossing, F.P., Free radicals by mass spectrometry. XLIII. Ionization potentials and ionic heats of formation for vinyl, allyl, and benzyl radicals, Can. J. Chem., 1971, 49, 357. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References

Symbols used in this document:

AE	Appearance energy
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
S°_liquid	Entropy of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.