Fluoroacetic acid


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
Δcliquid-170.85kcal/molCcbSwarts, 1919Not corrected for CODATA value of ΔfH

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 by: William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
12.5308.AStephenson and Malanowski, 1987Based on data from 293. to 443. K. See also Dykyj, 1970.
12.8308.TJasper and Miller, 1955Based on data from 293. to 443. K.

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: John E. Bartmess

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

FCH2CO2 anion + Hydrogen cation = Fluoroacetic acid

By formula: C2H2FO2- + H+ = C2H3FO2

Quantity Value Units Method Reference Comment
Δr339.0 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Δr338.7 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr338.5 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr331.6 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase
Δr331.3 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr331.0 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

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
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

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2F+13.4 ± 0.1CO2+HEIHolmes, Lossing, et al., 1983LBLHLM
CH3F+[CH2FH+]11.6 ± 0.2CO2EIHolmes, Lossing, et al., 1983LBLHLM

De-protonation reactions

FCH2CO2 anion + Hydrogen cation = Fluoroacetic acid

By formula: C2H2FO2- + H+ = C2H3FO2

Quantity Value Units Method Reference Comment
Δr339.0 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr338.7 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr338.5 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr331.6 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr331.3 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr331.0 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

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.
Origin B.Kimball ET AL.J.Chromatogr.,634,289(1993)
NIST MS number 281634

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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.

Swarts, 1919
Swarts, F., Etudes thermochimiques sur les combinaisons organiques fluorees, J. Chim. Phys., 1919, 17, 3-70. [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]

Jasper and Miller, 1955
Jasper, Joseph J.; Miller, George B., The Vapor Pressure of Monofluoroacetic Acid, J. Phys. Chem., 1955, 59, 5, 441-442, https://doi.org/10.1021/j150527a015 . [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]

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]

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]


Notes

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