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Acetic acid, chloro-

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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 as indicated in comments:
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltacsolid-174. ± 1.kcal/molCcbSmith, Bjellerup, et al., 1953ALS
Deltacsolid-173.7kcal/molCcbSchjanberg, 1935ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
43.00321.05Urazovskii and Sidorov, 1950T = 47 to 65°C. Value is unsmoothed experimental datum. Maxima at 50.7, 56.9, and 61.2°C.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
34.4288. - 318.Pickering, 1895T = 288 to 349 K.; DH

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, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil462.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil461.KN/ADreisbach and Martin, 1949Uncertainty assigned by TRC = 0.07 K; TRC
Tboil462.5KN/ALecat, 1943Uncertainty assigned by TRC = 0.3 K; TRC
Tboil462.5KN/ALecat, 1943, 2Uncertainty assigned by TRC = 0.35 K; TRC
Tboil462.50KN/ALecat, 1926Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus332. ± 7.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Deltasub19.6 ± 0.2kcal/molMELagoa, Diogo, et al., 2001AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
14.6351.AStephenson and Malanowski, 1987Based on data from 336. - 463. K.; AC
13.6392.AStephenson and Malanowski, 1987Based on data from 377. - 463. K. See also McDonald, Shrader, et al., 1959 and Dykyj, 1970.; AC
13.3411.N/ADreisbach and Shrader, 1949Based on data from 396. - 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)

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Temperature (K) A B C Reference
344.66 - 462.34.685161733.96-92.154McDonald, Shrader, et al., 1959

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
3.90334.8DSCLagoa, Diogo, et al., 2001AC
3.8948334.33N/APickering, 1895«alpha»-Isomer.; DH
3.3301329.16N/APickering, 1895«beta»-Isomer.; DH

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
11.65334.33Pickering, 1895«alpha»-Isomer.; DH
10.12329.16Pickering, 1895«beta»-Isomer.; DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 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

ClCH2CO2 anion + Hydrogen cation = Acetic acid, chloro-

By formula: C2H2ClO2- + H+ = C2H3ClO2

Quantity Value Units Method Reference Comment
Deltar336.5 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Deltar336.2 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar336.3 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar329.0 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Deltar328.8 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar328.8 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

Chlorine anion + Acetic acid, chloro- = (Chlorine anion bullet Acetic acid, chloro-)

By formula: Cl- + C2H3ClO2 = (Cl- bullet C2H3ClO2)

Quantity Value Units Method Reference Comment
Deltar14.1 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase; B
Quantity Value Units Method Reference Comment
Deltar7.8 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase; B

Water + Acetic acid, chloro-, methyl ester = Methyl Alcohol + Acetic acid, chloro-

By formula: H2O + C3H5ClO2 = CH4O + C2H3ClO2

Quantity Value Units Method Reference Comment
Deltar-13.70 ± 0.70kcal/molEqkGuthrie and Cullimore, 1980liquid phase; Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol; ALS

Water + Acetyl chloride, chloro- = Hydrogen chloride + Acetic acid, chloro-

By formula: H2O + C2H2Cl2O = HCl + C2H3ClO2

Quantity Value Units Method Reference Comment
Deltar-22.35kcal/molCmPritchard and Skinner, 1950liquid phase; Heat of hydrolysis at 298 K; ALS

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 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)182.9kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity175.5kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.7PEWatanabe, Yokoyama, et al., 1973LLK
10.99PEWatanabe, Yokoyama, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHO2+12.34CH2ClEIHolmes, Lossing, et al., 1991LL
CH3Cl+11.08 ± 0.05CO2EIHolmes, Lossing, et al., 1983LBLHLM

De-protonation reactions

ClCH2CO2 anion + Hydrogen cation = Acetic acid, chloro-

By formula: C2H2ClO2- + H+ = C2H3ClO2

Quantity Value Units Method Reference Comment
Deltar336.5 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Deltar336.2 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar336.3 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar329.0 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Deltar328.8 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar328.8 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

Ion clustering 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: 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

Chlorine anion + Acetic acid, chloro- = (Chlorine anion bullet Acetic acid, chloro-)

By formula: Cl- + C2H3ClO2 = (Cl- bullet C2H3ClO2)

Quantity Value Units Method Reference Comment
Deltar14.1 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase
Quantity Value Units Method Reference Comment
Deltar7.8 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase

IR Spectrum

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Data compiled by: Coblentz Society, Inc.


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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Mass spectrum
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Additional Data

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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 818

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UV/Visible spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Schurz and Ullrich, 1959
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. 12868
Instrument Frankfurt
Melting point 63
Boiling point 189.3

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H., Heats of combustion of organic chloro compounds determined by the "quartz wool" method, Acta Chem. Scand., 1953, 7, 65. [all data]

Schjanberg, 1935
Schjanberg, E., Die Verbrennungswarmen und die Refraktionsdaten einiger chlorsubstituierter Fettsauren und Ester., Z. Phys. Chem. Abt. A, 1935, 172, 197-233. [all data]

Urazovskii and Sidorov, 1950
Urazovskii, S.S.; Sidorov, I.A., Concerning singularities in the temperature dependence of the specific heat of liquids and the nature of phase transitions of the second kind, Doklady Akad. Nauk, 1950, SSSR 70, 859-862. [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]

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]

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]

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]

Schurz and Ullrich, 1959
Schurz, J.; Ullrich, A., Z. physik. Chem. (Frankfurt), 1959, 21, 185. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References