Acetic acid, chloro-
- Formula: C2H3ClO2
- Molecular weight: 94.497
- 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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Phase change data
Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 462.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 461. | K | N/A | Dreisbach and Martin, 1949 | Uncertainty assigned by TRC = 0.07 K; TRC |
Tboil | 462.5 | K | N/A | Lecat, 1943 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tboil | 462.5 | K | N/A | Lecat, 1943, 2 | Uncertainty assigned by TRC = 0.35 K; TRC |
Tboil | 462.50 | K | N/A | Lecat, 1926 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 332. ± 7. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 19.6 ± 0.2 | kcal/mol | ME | Lagoa, Diogo, et al., 2001 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
14.6 | 351. | A | Stephenson and Malanowski, 1987 | Based on data from 336. to 463. K.; AC |
13.6 | 392. | A | Stephenson and Malanowski, 1987 | Based on data from 377. to 463. K. See also McDonald, Shrader, et al., 1959 and Dykyj, 1970.; AC |
13.3 | 411. | N/A | Dreisbach and Shrader, 1949 | Based on data from 396. to 460. K. See also Dreisbach and Martin, 1949, 2.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
344.66 to 462.3 | 4.68516 | 1733.96 | -92.154 | McDonald, Shrader, et al., 1959 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
3.90 | 334.8 | DSC | Lagoa, Diogo, et al., 2001 | AC |
3.8948 | 334.33 | N/A | Pickering, 1895 | α-Isomer.; DH |
3.3301 | 329.16 | N/A | Pickering, 1895 | β-Isomer.; DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.65 | 334.33 | Pickering, 1895 | α-Isomer.; DH |
10.12 | 329.16 | Pickering, 1895 | β-Isomer.; DH |
Gas phase ion energetics data
Go To: Top, Phase change data, Ion clustering data, IR Spectrum, References, Notes
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:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 182.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 175.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.7 | PE | Watanabe, Yokoyama, et al., 1973 | LLK |
10.99 | PE | Watanabe, Yokoyama, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO2+ | 12.34 | CH2Cl | EI | Holmes, Lossing, et al., 1991 | LL |
CH3Cl+ | 11.08 ± 0.05 | CO2 | EI | Holmes, Lossing, et al., 1983 | LBLHLM |
De-protonation 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 |
Ion clustering data
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, 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: John E. Bartmess
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
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 |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 7.8 ± 2.0 | kcal/mol | IMRE | Larson and McMahon, 1985 | gas phase |
IR Spectrum
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLUTION (1% CCl4 FOR 3800-1330, 1% CS2 FOR 1330-400 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (11% IN CCl4 FOR 3800-1300, 4% IN CS2 FOR 1300-645, AND 11% IN CCl4 FOR 645-250 CM-1); PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm-1 resolution
References
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 2875-8. [all data]
Lecat, 1943
Lecat, M.,
Negative and other Azeotropes,
C. R. Hebd. Seances Acad. Sci., 1943, 217, 242. [all data]
Lecat, 1943, 2
Lecat, M.,
Azeotropes of Ethyl Urethane and other Azeotropes,
C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]
Lecat, 1926
Lecat, M.,
New binary azeotropes: 3rd list,
Ann. Soc. Sci. Bruxelles, Ser. B, 1926, 45, 284-94. [all data]
Lagoa, Diogo, et al., 2001
Lagoa, Ana L.C.; Diogo, Hermínio P.; Dias, M. Pilar; Minas da Piedade, Manuel E.; Amaral, Luísa M.P.F.; Ribeiro da Silva, Manuel A.V.; Martinho Simões, José A.; Guedes, Rita C.; Costa Cabral, Benedito J.; Schwarz, Karsten; Epple, Matthias,
Energetics of C-Cl, C-Br, and C-I Bonds in Haloacetic Acids: Enthalpies of Formation of XCH2COOH (X=Cl, Br, I) Compounds and the Carboxymethyl Radical,
Chem. Eur. J., 2001, 7, 2, 483-489, https://doi.org/10.1002/1521-3765(20010119)7:2<483::AID-CHEM483>3.0.CO;2-A
. [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]
McDonald, Shrader, et al., 1959
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]
Dykyj, 1970
Dykyj, J.,
Petrochemica, 1970, 10, 2, 51. [all data]
Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A.,
Vapor Pressure--Temperature Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054
. [all data]
Dreisbach and Martin, 1949, 2
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053
. [all data]
Pickering, 1895
Pickering, S.U.,
A comparison of some properties of acetic acid and its chloro- and bromo-derivatives,
J. Chem. Soc., 1895, 67, 664-684. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Watanabe, Yokoyama, et al., 1973
Watanabe, I.; Yokoyama, Y.; Ikeda, S.,
Lone pair ionization potentials of carboxylic acids determined by He(I) photoelectron spectroscopy,
Bull. Chem. Soc. Jpn., 1973, 46, 1959. [all data]
Holmes, Lossing, et al., 1991
Holmes, J.L.; Lossing, F.P.; Mayer, P.M.,
Heats of formation of oxygen-containing organic free radicals from appearance energy measurements,
J. Am. Chem. Soc., 1991, 113, 9723. [all data]
Holmes, Lossing, et al., 1983
Holmes, J.L.; Lossing, F.P.; Terlouw, J.K.; Burgers, P.C.,
Novel gas-phase ions. The radical cations [CH2XH]+. (X = F, Cl, Br, I, OH, NH2, SH) and [CH2CH2NH3]+.,
Can. J. Chem., 1983, 61, 2305. [all data]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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