Ethylene, 1,2-dichloro-, (Z)-
- Formula: C2H2Cl2
- Molecular weight: 96.943
- IUPAC Standard InChIKey: KFUSEUYYWQURPO-UPHRSURJSA-N
- CAS Registry Number: 156-59-2
- 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. - Stereoisomers:
- Other names: Ethene, 1,2-dichloro-, (Z)-; (Z)-1,2-Dichloroethylene; cis-Di-1,2-Chloroethylene; cis-Dichloroethylene; cis-1,2-Dichloroethene; cis-1,2-Dichloroethylene; 1,2-cis-Dichloroethylene; (Z)-CHCl=CHCl; (Z)-1,2-Dichloroethene; 1,2-cis-Dichloroethene; Acetylene dichloride, cis-; 1,cis-2-Dichloroethene; Ethylene, 1,2-dichloro-, cis-; Ethene, 1,2-dichloro-, (1Z)-; HCC 1130c; R 1130c
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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 | -0.7 ± 0.5 | kcal/mol | Review | Manion, 2002 | based on measurements by 1974RLV of equilbrium with 1,1-dichloroethane; DRB |
ΔfH°gas | 1.02 | kcal/mol | Eqk | Rozhnov, Levanova, et al., 1974 | ALS |
ΔfH°gas | 0.8 | kcal/mol | Cm | Kirkbride, 1956 | Heat of chlorination; 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 | -8.15 ± 0.53 | kcal/mol | Review | Manion, 2002 | derived from recommended ΔfHgas° and ΔvapH°; DRB |
ΔfH°liquid | -6.8 | kcal/mol | Cm | Kirkbride, 1956 | Heat of chlorination; ALS |
ΔfH°liquid | -3.289 | kcal/mol | Eqk | Pitzer and Hollenberg, 1954 | Heat of isomerization at 0K; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -261.4 ± 2.0 | kcal/mol | Ccb | Smith, Bjellerup, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -261. ± 2. kcal/mol; ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
27.20 | 288. | Mehl, 1934 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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: C2H2Cl2 = C2H2Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.48 | kcal/mol | Eqk | Rozhnov, Levanova, et al., 1974 | liquid phase; GC |
ΔrH° | -0.72 ± 0.16 | kcal/mol | Eqk | Craig, Piper, et al., 1971 | gas phase |
ΔrH° | 0.723 | kcal/mol | Eqk | Wood and Stevenson, 1941 | gas phase; Heat of isomerization |
ΔrH° | 0.62 | kcal/mol | Eqk | Maroney, 1935 | gas phase; At 300-975 K |
By formula: C2H2Cl2 = C2H2Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 0.2 | kcal/mol | Kin | Laursen and Pimentel, 1989 | gas phase; Photolysis |
ΔrH° | 0.44 ± 0.09 | kcal/mol | Eqk | Craig, Piper, et al., 1971 | gas phase |
ΔrH° | 0.445 ± 0.020 | kcal/mol | Eqk | Pitzer and Hollenberg, 1954 | liquid phase; Heat of isomerization at 0K |
By formula: C2H2Cl2 = C2H2Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.32 | kcal/mol | Eqk | Rozhnov, Levanova, et al., 1974 | liquid phase; solvent: Dichloromethylene; GC |
By formula: C2H2Cl2 + Cl2 = C2H2Cl4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -40.4 | kcal/mol | Cm | Kirkbride, 1956 | liquid phase; Heat of chlorination |
By formula: C2H2Cl2 = H2 + C2Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 3.9 | kcal/mol | Kin | Laursen and Pimentel, 1989 | gas phase; Photolysis |
By formula: C2H2Cl2 = C2HCl + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 2.3 | kcal/mol | Kin | Laursen and Pimentel, 1989 | gas phase; Photolysis |
By formula: C2H2Cl2 = C2H2 + Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 5.1 | kcal/mol | Kin | Laursen and Pimentel, 1989 | gas phase; Photolyses |
By formula: C2H2Cl2 + HCl = C2H3Cl3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -14.6 | kcal/mol | Cm | Levanova, Treger, et al., 1975 | liquid phase |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.66 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.65 | PE | Lake and Thompson, 1970 | RDSH |
9.68 | PE | Jonathan, Ross, et al., 1970 | RDSH |
9.66 | S | Walsh and Warsop, 1968 | RDSH |
9.65 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.66 ± 0.02 | PI | Momigny, 1960 | RDSH |
9.65 | PI | Bralsford, Harris, et al., 1960 | RDSH |
9.8 | PE | Von Niessen, Asbrink, et al., 1982 | Vertical value; LBLHLM |
9.80 | PE | Wittel and Bock, 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2HCl+ | 13.27 ± 0.05 | HCl | EI | Momigny, 1961 | RDSH |
C2H2Cl+ | 12.29 ± 0.05 | Cl | EI | Momigny, 1961 | RDSH |
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]
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]
Kirkbride, 1956
Kirkbride, F.W.,
The heats of chlorination of some hydrocarbons and their chloro-derivatives,
J. Appl. Chem., 1956, 6, 11-21. [all data]
Pitzer and Hollenberg, 1954
Pitzer, K.S.; Hollenberg, J.L.,
Cis- and trans-dichloroethylenes. The infrared spectra from 130-400 cm.-1 and the thermodynamic properties,
J. Am. Chem. Soc., 1954, 76, 1493-1496. [all data]
Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H.,
Heats of combustion of organic chloro compounds determined by the "quartz wool" method,
Acta Chem. Scand., 1953, 7, 65. [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]
Mehl, 1934
Mehl, W.,
Die spezifische Wärme einiger flüssiger Kältemittel,
Z. ges. Kalte-Ind., 1934, 41, 152-153. [all data]
Craig, Piper, et al., 1971
Craig, N.C.; Piper, L.G.; Wheeler, V.L.,
Thermodynamics of cis-trans isomerizations. II. The 1-chloro-2-fluoroethylenes, 1,2-difluorocyclopropanes, and related molecules,
J. Phys. Chem., 1971, 75, 1453-1460. [all data]
Wood and Stevenson, 1941
Wood, R.E.; Stevenson, D.P.,
The energy of isomerization of cis- and trans-dichloroethylene,
J. Am. Chem. Soc., 1941, 63, 1650-1653. [all data]
Maroney, 1935
Maroney, W.,
The thermal equilibrium of the cis-trans isomers of dichloroethylene at high temperatures,
J. Am. Chem. Soc., 1935, 57, 2397-2398. [all data]
Laursen and Pimentel, 1989
Laursen, S.L.; Pimentel, G.C.,
Matrix-induced intersystem crossing in the photochemistry of the 1,2-dichloroethenes,
J. Phys. Chem., 1989, 93, 2328-2333. [all data]
Levanova, Treger, et al., 1975
Levanova, S.V.; Treger, Yu.A.; Velichko, S.M.; Rozhnov, A.M.; Khlestkov, A.I.; Pisarev, V.V.,
Liquid-phase hydrochlorination of symmetrical dichloroethylenes,
J. Appl. Chem. USSR, 1975, 48, 1628-1631, In original 1574. [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 and Warsop, 1968
Walsh, A.D.; Warsop, P.A.,
Ultra-violet absorption spectrum of cis-1,2-dichloro ethylene,
J. Chem. Soc. Faraday Trans., 1968, 64, 1418. [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]
Momigny, 1960
Momigny, J.,
Les potentials d'ionisation des dihalogenoethylenes cis et trans,
Bull. Classe Sci. Acad. Roy. Belg., 1960, 46, 686. [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]
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]
Momigny, 1961
Momigny, J.,
Comportement des dihalogenoethylenes cis et trans sous l'impact electronique,
Bull. Soc. Chim. Belges, 1961, 70, 241. [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 Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy 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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