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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase ion energetics data
Go To: Top, Gas Chromatography, 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) | 170.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 162.7 | kcal/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° | 323.8 ± 2.9 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 322.8 ± 2.9 | kcal/mol | G+TS | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 322.8 ± 4.1 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 317.4 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 316.4 ± 2.0 | kcal/mol | IMRE | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 316.3 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
Gas Chromatography
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 744. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Capillary | OV-101 | 730. | Zenkevich and Rodin, 2002 | Nitrogen, 60. C @ 0. min, 4. K/min, 240. C @ 0. min; Column length: 25. m; Column diameter: 0.25 mm |
References
Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Zenkevich and Rodin, 2002
Zenkevich, I.G.; Rodin, A.A.,
Gas Chromatographic One-Step Determination of Number of Hydroxyl Groups in Polyphenols with Mixed Derivatization Reagents,
Zh. Anal. Khim. (Rus.), 2002, 57, 7, 732-736. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.