Ethene, 1,1-dichloro-
- Formula: C2H2Cl2
- Molecular weight: 96.943
- IUPAC Standard InChI: InChI=1S/C2H2Cl2/c1-2(3)4/h1H2
- IUPAC Standard InChIKey: LGXVIGDEPROXKC-UHFFFAOYSA-N
- CAS Registry Number: 75-35-4
- 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, 1,1-dichloro-; Vinylidene chloride; 1,1-Dichloroethene; 1,1-Dichloroethylene; CH2=CCl2; Chlorure de vinylidene; 1,1-DCE; NCI-C54262; Rcra waste number U078; VDC; Vinylidene dichloride; Vinylidine chloride; 1,1-dichloroethylene (vinylidine chloride); 1,1-dichloroethylene (vinylidene chloride)
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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 |
|---|---|---|---|---|---|
| ΔfH°gas | 2. ± 2. | kJ/mol | Review | Manion, 2002 | derived from recommended ΔfHliquid° and ΔvapH°; DRB |
| ΔfH°gas | 2.2 ± 1.4 | kJ/mol | Ccr | Mansson, Ringner, et al., 1971 | ALS |
Condensed phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -24. ± 2. | kJ/mol | Review | Manion, 2002 | weighted average of several measurements; DRB |
| ΔfH°liquid | -24.3 ± 1.4 | kJ/mol | Ccr | Mansson, Ringner, et al., 1971 | ALS |
| ΔfH°liquid | -25. ± 1. | kJ/mol | Ccb | Sinke and Stull, 1958 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1096.0 ± 1.4 | kJ/mol | Ccr | Mansson, Ringner, et al., 1971 | ALS |
| ΔcH°liquid | -1095.9 | kJ/mol | Ccb | Sinke and Stull, 1958 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 201.54 | J/mol*K | N/A | Hildenbrand, McDonald, et al., 1959 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 111.29 | 298.15 | Hildenbrand, McDonald, et al., 1959 | T = 13 to 290 K.; DH |
Reaction thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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
=
+
By formula: C2H3Cl3 = C2H2Cl2 + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 56.9 | kJ/mol | Eqk | Levanova, Bushneva, et al., 1979 | liquid phase |
| ΔrH° | 49.0 | kJ/mol | Eqk | Levanova, Bushneva, et al., 1979 | gas phase |
| ΔrH° | 56.9 ± 2.1 | kJ/mol | Eqk | Levanova, Treger, et al., 1975 | liquid phase; solvent: Nitrobenzene; Flow reactor at 50°C |
=
+
By formula: C2H3Cl3 = C2H2Cl2 + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 51.5 | kJ/mol | Eqk | Levanova, Bushneva, et al., 1979 | gas phase |
| ΔrH° | 65.3 | kJ/mol | Eqk | Levanova, Bushneva, et al., 1979 | liquid phase |
+
=
By formula: C2H2Cl2 + HCl = C2H3Cl3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -54.64 ± 0.84 | kJ/mol | Eqk | Hu, Sinke, et al., 1972 | gas phase; Heat of halogenation at 348-399 K |
=
By formula: C2H2Cl2 = C2H2Cl2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -5.52 | kJ/mol | Eqk | Rozhnov, Levanova, et al., 1974 | liquid phase; solvent: Dichloromethylene; GC |
=
By formula: C2H2Cl2 = C2H2Cl2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -3.5 | kJ/mol | Eqk | Rozhnov, Levanova, et al., 1974 | liquid phase; solvent: Dichloroethylene; GC |
Gas phase ion energetics data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
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
B - John E. Bartmess
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 9.81 ± 0.04 | eV | N/A | N/A | L |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 0.099999 | ECD | Wiley, Chen, et al., 1991 | B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.83 | PE | Lake and Thompson, 1970 | RDSH |
| 9.74 | PE | Jonathan, Ross, et al., 1970 | RDSH |
| 9.86 | S | Walsh, Warsop, et al., 1968 | RDSH |
| 9.79 | PI | Bralsford, Harris, et al., 1960 | RDSH |
| 10.0 | PE | Von Niessen, Asbrink, et al., 1982 | Vertical value; LBLHLM |
| 9.99 ± 0.02 | PE | Bunzli, Frost, et al., 1976 | Vertical value; LLK |
| 10.00 | PE | Wittel and Bock, 1974 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Mansson, Ringner, et al., 1971
Mansson, M.; Ringner, B.; Sunner, S.,
The enthalpies of combustion and formation of some simple chloroalkanes and chloralkenes 1,1,1-trichloroethane and 1,1-dichloroethene,
J. Chem. Thermodyn., 1971, 3, 547-551. [all data]
Sinke and Stull, 1958
Sinke, G.C.; Stull, D.R.,
Heats of combustion of some organic compounds containing chlorine,
J. Phys. Chem., 1958, 62, 397-401. [all data]
Hildenbrand, McDonald, et al., 1959
Hildenbrand, d.L.; McDonald, R.A.; Kramer, W.R.; Stull, D.R.,
Thermodynamic and spectroscopic study of vinylidene chloride. I. Thermodynamic properties of the solid, liquid, and ideal gas,
J. Chem. Phys., 1959, 30, 930-934. [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]
Levanova, Treger, et al., 1975
Levanova, S.V.; Treger, Yu.A.; Velichko, S.M.; Rozhnov, A.M.; Bshneva, L.I.; Talanov, A.I.,
Equilibrium of the vinylidene chloride-methylchloroform system,
Zh. Prikl. Khim. (Leningrad), 1975, 42, 480-481. [all data]
Hu, Sinke, et al., 1972
Hu, A.T.; Sinke, G.C.; Mintz, M.J.,
The enthalpy of formation of 1,1,1-trichloroethane from enthalpy of combustion and equilibrium studies,
J. Chem. Thermodyn., 1972, 4, 239-245. [all data]
Rozhnov, Levanova, et al., 1974
Rozhnov, A.M.; Levanova, S.V.; Dvornikova, G.A.; Sadovnikova, S.L.,
Equilibrium of isomerization of dichloroethylenes,
J. Appl. Chem. USSR, 1974, 47, 667-669. [all data]
Wiley, Chen, et al., 1991
Wiley, J.R.; Chen, E.C.M.; Chen, E.S.D.; Richardson, P.; Reed, W.R.; Wentworth, W.E.,
The Determination of Absolute Electron Affinities of Chlorobenzenes, Chloronaphthalenes and Chlorinated Biphenyls from Reduction Potentials,
J. Electroanal. Chem. Interfac., 1991, 307, 1-2, 169, https://doi.org/10.1016/0022-0728(91)85546-2
. [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]
Jonathan, Ross, et al., 1970
Jonathan, N.; Ross, K.; Tomlinson, V.,
The photoelectron spectra of dichloroethylenes,
Intern. J. Mass Spectrom. Ion Phys., 1970, 4, 51. [all data]
Walsh, Warsop, et al., 1968
Walsh, A.D.; Warsop, P.A.; Whiteside, J.A.B.,
Ultra-violet absorption spectrum of 1,1-dichloro ethylene,
J. Chem. Soc. Faraday Trans., 1968, 64, 1432. [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]
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]
Bunzli, Frost, et al., 1976
Bunzli, J.C.; Frost, D.C.; Herring, F.G.; McDowell, C.A.,
Assignment of the doublet states arising from ionization of chlorine lone-pairs in molecules possessing C2v symmetry,
J. Electron Spectrosc. Relat. Phenom., 1976, 9, 289. [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]
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:
Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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