Oxalyl chloride
- Formula: C2Cl2O2
- Molecular weight: 126.926
- IUPAC Standard InChI: InChI=1S/C2Cl2O2/c3-1(5)2(4)6
- IUPAC Standard InChIKey: CTSLXHKWHWQRSH-UHFFFAOYSA-N
- CAS Registry Number: 79-37-8
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Ethanedioyl dichloride; Ethanedioyl chloride; Oxalic acid dichloride; Oxalic dichloride; Oxaloyl chloride; Oxalyl dichloride; (COCl)2
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -335.8 ± 6.3 | kJ/mol | Ccr | Walker and Prophet, 1967 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -326. ± 5.9 kJ/mol |
Condensed phase thermochemistry data
Go To: Top, Gas 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -367.6 ± 4.7 | kJ/mol | Ccr | Walker and Prophet, 1967 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -358. ± 2. kJ/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -417. ± 2. | kJ/mol | Ccr | Walker and Prophet, 1967 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LL - Sharon G. Lias and Joel F. Liebman
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.91 ± 0.05 | PE | Frost, McDowell, et al., 1977 | LLK |
| 11.33 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
| 11.26 | PE | Meeks and McGlynn, 1975 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C2O2+ | 15.7 ± 0.1 | Cl2 | EI | Chen and Holmes, 1994 | LL |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase 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.
Walker and Prophet, 1967
Walker, L.C.; Prophet, H.,
Enthalpy of formation of oxalyl chloride and the COCl radical,
Trans. Faraday Soc., 1967, 63, 879-882. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Frost, McDowell, et al., 1977
Frost, D.C.; McDowell, C.A.; Pouzard, G.; Westwood, N.P.C.,
The photoelectron spectra of the oxalyl halides (COX)2,[X = F, Cl and Br],
J. Electron Spectrosc. Relat. Phenom., 1977, 10, 273. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Meeks and McGlynn, 1975
Meeks, J.L.; McGlynn, S.P.,
Photoelectron spectra of carbonyls. Oxalyl chloride, ethyl oxalyl chloride, ethyl oxamate and N,N-dimethyl ethyl oxamate,
Spectrosc. Lett., 1975, 8, 439. [all data]
Chen and Holmes, 1994
Chen, H.; Holmes, J.L.,
The generation of OC2O+ and OC2O and a study of ionized OC3O and C2O by tandem mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1994, 133, 111. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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