Trifluoroacetic acid
- Formula: C2HF3O2
- Molecular weight: 114.0233
- IUPAC Standard InChIKey: DTQVDTLACAAQTR-UHFFFAOYSA-N
- CAS Registry Number: 76-05-1
- 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, trifluoro-; Perfluoroacetic acid; Trifluoroethanoic acid; CF3COOH; Kyselina trifluoroctova; Trifluoracetic acid; UN 2699; Acetic acid, 2,2,2-trifluoro-; NSC 77366
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -1069.9 ± 1.5 | kJ/mol | Ccr | Kolesov, Slavutskaya, et al., 1972 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -1060. ± 2. kJ/mol; see Kolesov and Zenkov, 1966 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -397.2 ± 1.5 | kJ/mol | Ccr | Kolesov, Slavutskaya, et al., 1972 | see Kolesov and Zenkov, 1966 |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 347. | K | N/A | Farchan Laboratories, 1990 | BS |
Tboil | 347. | K | N/A | PCR Inc., 1990 | BS |
Tboil | 345.6 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 345.1 | K | N/A | Malijevska, Sysova, et al., 1986 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tboil | 345.7 | K | N/A | Parnes, Khotimskaya, et al., 1969 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 531.17 | K | N/A | Kohler, Atrops, et al., 1981 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 288.43 | K | N/A | Parnes, Khotimskaya, et al., 1969 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 41. ± 3. | kJ/mol | E | Guthrie, 1976 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
35.9 | 300. | A | Stephenson and Malanowski, 1987 | Based on data from 285. to 345. K. See also Kreglewski, 1962, Dykyj, 1970, and Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
285. to 344.80 | 3.34534 | 1267.252 | -52.958 | Kreglewski, 1962, 2 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 11.5 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 711.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 680.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.6 | PE | Asbrink, Svensson, et al., 1981 | LLK |
11.46 | PE | Sweigart and Turner, 1972 | LLK |
12.0 | PE | Asbrink, Svensson, et al., 1981 | Vertical value; LLK |
12.06 | PE | Carnovale, Gan, et al., 1980 | Vertical value; LLK |
12.08 ± 0.05 | PE | Coleman, Green, et al., 1979 | Vertical value; LLK |
12.00 | PE | Watanabe, Yokoyama, et al., 1973 | Vertical value; LLK |
12.00 ± 0.03 | PE | Thomas, 1972 | Vertical value; LLK |
De-protonation reactions
By formula: C2F3O2- + H+ = C2HF3O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1355. ± 12. | kJ/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 1351. ± 12. | kJ/mol | G+TS | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1351. ± 17. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1328. ± 8.4 | kJ/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 1324. ± 8.4 | kJ/mol | IMRE | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1323. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | 1851 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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.
Kolesov, Slavutskaya, et al., 1972
Kolesov, V.P.; Slavutskaya, G.M.; Papina, T.S.,
Standard enthalpies of formation of perfluorodi-n-butyl ether and trifluoroacetic acid,
Russ. J. Phys. Chem. (Engl. Transl.), 1972, 46, 474. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Kolesov and Zenkov, 1966
Kolesov, V.P.; Zenkov, I.D.,
Standard of enthalpy of formation of trifluoroacetic acid,
Russ. J. Phys. Chem. (Engl. Transl.), 1966, 40, 743-744. [all data]
Farchan Laboratories, 1990
Farchan Laboratories,
Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]
PCR Inc., 1990
PCR Inc.,
Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Malijevska, Sysova, et al., 1986
Malijevska, I.; Sysova, M.; Vlckova, D.,
Vapour-Liquid Equilibrium in Strongly Associated Systems. The Systems Acetic Acid-Propionic Acid and Acetic Acid-Trifluoroacetic Acid,
Collect. Czech. Chem. Commun., 1986, 51, 194. [all data]
Parnes, Khotimskaya, et al., 1969
Parnes, Z.N.; Khotimskaya, G.A.; Kudryavtsev, R.V.; Lukina, M.Y.; Kursanov, D.N.,
The Behavior of Cyclopropane Hydrocarbons in Ionic Hydrogenation Reactions,
Dokl. Akad. Nauk SSSR, Ser. Khim., 1969, 184, 615-8. [all data]
Kohler, Atrops, et al., 1981
Kohler, F.; Atrops, H.; Kalali, H.; Liebermann, E.; Wilhelm, E.; Ratkovics, F.; Salamon, T.,
Molecular Interactions in Mistures of Carboxylic Acids with Amines 1. Melting Curves adn Viscosities,
J. Phys. Chem., 1981, 85, 2520-4. [all data]
Guthrie, 1976
Guthrie, J.P.,
Thermodynamics of ester and orthoester formation from trifluoroacetic acid,
Can. J. Chem., 1976, 54, 202-209. [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]
Kreglewski, 1962
Kreglewski, A.,
Bull. Pol. Acad. Sci., Ser. Sci. Chem., 1962, 10, 629. [all data]
Dykyj, 1970
Dykyj, J.,
Petrochemica, 1970, 10, 2, 51. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Kreglewski, 1962, 2
Kreglewski, A.,
Vapour Pressures and Molar Volumes of Liquid Perfluoro-n-Octane Trifluoracetic Acid, and its Anhydride,
Bull. Acad. Pol. Sci. Ser. Sci. Chim., 1962, 10, 11-12, 629-633. [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]
Asbrink, Svensson, et al., 1981
Asbrink, L.; Svensson, A.; Von Niessen, W.; Bieri, G.,
30.4 nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1981, 24, 293. [all data]
Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W.,
Lone pair orbitals and their interactions studied by photoelectron spectroscopy. I. Carboxylic acids and their derivatives,
J. Am. Chem. Soc., 1972, 94, 5592. [all data]
Carnovale, Gan, et al., 1980
Carnovale, F.; Gan, T.H.; Peel, J.B.,
Photoelectron spectroscopic studies of the monomers and dimers of acetic and trifluoracetic acids,
J. Electron Spectrosc. Relat. Phenom., 1980, 20, 53. [all data]
Coleman, Green, et al., 1979
Coleman, A.W.; Green, J.C.; Hayes, A.J.; Seddon, E.A.; Lloyd, D.R.; Niwa, Y.,
A comparison of the electronic structure of some group 6A dimetal tetracarboxylates using photoelectron spectroscopy,
J. Chem. Soc. Dalton Trans., 1979, 75, 1057. [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]
Thomas, 1972
Thomas, R.K.,
Photoelectron spectroscopy of hydrogen-bonded systems: spectra of monomers, dimers and mixed complexes of carboxylic acides,
Proc. R. Soc. London A:, 1972, 331, 249. [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]
Jinfeng, Topsom, et al., 1988
Jinfeng, C.; Topsom, R.D.; Headley, A.D.; Koppel, I.; Mishima, M.; Taft, R.W.; Veji, S.,
Acidities of Substituted Acetic Acids,
J. Mol. Struct., 1988, 168, 141, https://doi.org/10.1016/0166-1280(88)80349-X
. [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, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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