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 | -80.3 ± 1.5 | kcal/mol | Ccr | Walker and Prophet, 1967 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -78.0 ± 1.4 kcal/mol |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -87.9 ± 1.1 | kcal/mol | Ccr | Walker and Prophet, 1967 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -85.6 ± 0.5 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -99.7 ± 0.5 | kcal/mol | Ccr | Walker and Prophet, 1967 |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 7.6 ± 0.9 | kcal/mol | E | Walker and Prophet, 1967 | ALS |
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference | Comment |
|---|---|---|---|
| 336.7 | 1.00 | Aldrich Chemical Company Inc., 1990 | BS |
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 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 |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| NIST MS number | 2589 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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| Source | Saksena and Kagarise, 1951 |
|---|---|
| Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
| Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
| Source reference | RAS UV No. 10174 |
| State | <none> |
| Instrument | Beckman quartz spectrophotometer |
| Melting point | - 12 |
| Boiling point | 63.5-64/ 763 mm |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, NIST Free Links, 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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Saksena and Kagarise, 1951
Saksena, B.D.; Kagarise, R.E.,
J. Chem. Phys., 1951, 19, 999. [all data]
Notes
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- Symbols used in this document:
AE Appearance energy Tboil Boiling point 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 ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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