Acetic acid, chloro-
- Formula: C2H3ClO2
- Molecular weight: 94.497
- IUPAC Standard InChI: InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
- IUPAC Standard InChIKey: FOCAUTSVDIKZOP-UHFFFAOYSA-N
- CAS Registry Number: 79-11-8
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: α-Chloroacetic acid; Chloroacetic acid; Chloroethanoic acid; Monochloroethanoic acid; CH2ClCOOH; Chloracetic acid; Monochloracetic acid; Monochloroacetic acid; Acide chloracetique; Acidomonocloroacetico; Monochloorazijnzuur; Monochloressigsaeure; MCA; Acide monochloracetique; Kyselina chloroctova; NCI-C60231; UN 1751; Acetic acid, 2-chloro-; NSC 142
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Reaction thermochemistry data
Go To: Top, 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:
B - John E. Bartmess
ALS - 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: C2H2ClO2- + H+ = C2H3ClO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 336.5 ± 2.2 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
| ΔrH° | 336.2 ± 2.2 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 336.3 ± 2.9 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 329.0 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
| ΔrG° | 328.8 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 328.8 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
+
= (
•
)
By formula: Cl- + C2H3ClO2 = (Cl- • C2H3ClO2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14.1 ± 2.0 | kcal/mol | IMRE | Larson and McMahon, 1985 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 7.8 ± 2.0 | kcal/mol | IMRE | Larson and McMahon, 1985 | gas phase; B |
+
=
+
By formula: H2O + C3H5ClO2 = CH4O + C2H3ClO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -13.70 ± 0.70 | kcal/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase; Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol; ALS |
+
=
+
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; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P.,
Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria,
Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092
. [all data]
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Larson and McMahon, 1985
Larson, J.W.; McMahon, T.B.,
Fluoride and chloride affinities of the main group oxides, fluorides, oxofluorides, and alkyls. Quantitative scales of lewis acidities from ICR halide exchange equilibria,
J. Am. Chem. Soc., 1985, 107, 766. [all data]
Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A.,
Effect of the acyl substituent on the equilibrium constant for hydration of esters,
Can. J. Chem., 1980, 58, 1281-1294. [all data]
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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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