Fluoroacetic acid
- Formula: C2H3FO2
- Molecular weight: 78.0424
- IUPAC Standard InChI: InChI=1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)
- IUPAC Standard InChIKey: QEWYKACRFQMRMB-UHFFFAOYSA-N
- CAS Registry Number: 144-49-0
- 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: Acetic acid, fluoro-; Cymonic acid; Fluoroethanoic acid; Gifblaar poison; HFA; Monofluoroacetic acid; CH2FCOOH; Acide-monofluoracetique; Acido monofluoroacetio; 2-Fluoroacetic acid; Monofluorazijnzuur; Monofluoressigsaure; UN 2642; Acetic acid, 2-fluoro-
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Phase change data
Go To: Top, Gas phase ion energetics data, 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: William E. Acree, Jr., James S. Chickos
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 12.5 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 293. to 443. K. See also Dykyj, 1970. |
| 12.8 | 308. | T | Jasper and Miller, 1955 | Based on data from 293. to 443. K. |
Gas phase ion energetics data
Go To: Top, Phase change data, 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
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 |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| CH2F+ | 13.4 ± 0.1 | CO2+H | EI | Holmes, Lossing, et al., 1983 | LBLHLM |
| CH3F+[CH2FH+] | 11.6 ± 0.2 | CO2 | EI | Holmes, Lossing, et al., 1983 | LBLHLM |
De-protonation reactions
+
=
By formula: C2H2FO2- + H+ = C2H3FO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 339.0 ± 2.2 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
| ΔrH° | 338.7 ± 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° | 338.5 ± 2.9 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 331.6 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
| ΔrG° | 331.3 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 331.0 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔrG° Free energy of reaction 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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