Acetyl chloride, chloro-
- Formula: C2H2Cl2O
- Molecular weight: 112.943
- IUPAC Standard InChIKey: VGCXGMAHQTYDJK-UHFFFAOYSA-N
- CAS Registry Number: 79-04-9
- 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: α-Chloroacetyl chloride; Chloracetyl chloride; Chloroacetic acid chloride; Chloroacetic chloride; Chloroacetyl chloride; Monochloroacetyl chloride; CH2ClCOCl; Chloroethanoyl chloride; Chlorid kyseliny chloroctove; Chlorure de chloracetyle; UN 1752; Acetyl chloride, 2-chloro-
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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 | -58.7 ± 2.1 | kcal/mol | Cm | Pritchard and Skinner, 1950 | Reanalyzed by Cox and Pilcher, 1970, Original value = -62.1 kcal/mol; Heat of hydrolysis at 298 K |
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 | -68.0 ± 2.0 | kcal/mol | Cm | Pritchard and Skinner, 1950 | Reanalyzed by Cox and Pilcher, 1970, Original value = -70.12 kcal/mol; Heat of hydrolysis at 298 K |
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
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 379. ± 3. | K | AVG | N/A | Average of 14 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 377. | K | N/A | Tulecki and Osinska, 1976 | TRC |
Tfus | 251.38 | K | N/A | McDonald, Shrader, et al., 1959 | Uncertainty assigned by TRC = 0.07 K; TRC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.8 | 268. | A | Stephenson and Malanowski, 1987 | Based on data from 253. to 379. K. See also Dykyj, 1970.; AC |
9.75 | 316. | N/A | McDonald, Shrader, et al., 1959, 2 | Based on data from 301. to 380. K.; AC |
10.5 | 305. | N/A | Kireev and Popov, 1935 | Based on data from 290. to 373. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
301.48 to 380.22 | 4.25330 | 1331.94 | -65.974 | McDonald, Shrader, et al., 1959, 2 |
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: H2O + C2H2Cl2O = HCl + C2H3ClO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -22.35 | kcal/mol | Cm | Pritchard and Skinner, 1950 | liquid phase; Heat of hydrolysis at 298 K |
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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.30 | PE | Katsumata and Kimura, 1975 | Vertical value |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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
View image of digitized spectrum (can be printed in landscape orientation).
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. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1992 |
NIST MS number | 125295 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pritchard and Skinner, 1950
Pritchard, H.O.; Skinner, H.A.,
The heats of hydrolysis of the chloro-substituted acetyl chlorides,
J. Chem. Soc., 1950, 272-276. [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]
Tulecki and Osinska, 1976
Tulecki, J.; Osinska, Z.,
Search for New Radioactive Agent XXIV. Synthesis of Some Sulfenomides Derived from Phenthiazine,
Ann. Phar, (Poznan), 1976, 12, 11-12. [all data]
McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R.,
Vapor Pressures and Freezing Points of 30 Organics,
J. Chem. Eng. Data, 1959, 4, 311. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Dykyj, 1970
Dykyj, J.,
Petrochemica, 1970, 10, 2, 51. [all data]
McDonald, Shrader, et al., 1959, 2
McDonald, R.A.; Shrader, S.A.; Stull, D.R.,
Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds.,
J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009
. [all data]
Kireev and Popov, 1935
Kireev, V.A.; Popov, A.A.,
Russ. J. Gen. Chem., 1935, 5, 1399. [all data]
Katsumata and Kimura, 1975
Katsumata, S.; Kimura, K.,
Photoelectron spectra and sum rule consideration. Effect of chlorine substitution on ionization energies for chloroethanes, chloroacetaldehydes and chloroacetyl chlorides,
J. Electron Spectrosc. Relat. Phenom., 1975, 6, 309. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point 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 ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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