Trifluoroacetic acid

• Formula: C₂HF₃O₂
• Molecular weight: 114.0233
• IUPAC Standard InChI: InChI=1S/C2HF3O2/c3-2(4,5)1(6)7/h(H,6,7) Copy

  
• IUPAC Standard InChIKey: DTQVDTLACAAQTR-UHFFFAOYSA-N Copy
• 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:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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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
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

Ionization energy determinations

De-protonation reactions

 +  =

By formula: C₂F₃O₂^- + H⁺ = C₂HF₃O₂

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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C₂H₂F₃O₂⁺ +  = (C₂H₂F₃O₂⁺ • )

By formula: C₂H₂F₃O₂⁺ + C₂HF₃O₂ = (C₂H₂F₃O₂⁺ • C₂HF₃O₂)

Bond type: Hydrogen bonds of the type OH-O between organics

References

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, Notes

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

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]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Cunningham, Payzant, et al., 1972
Cunningham, A.J.; Payzant, J.D.; Kebarle, P., A Kinetic Study of the Proton Hydrate H+(H2O)n Equilibria in the Gas Phase, J. Am. Chem. Soc., 1972, 94, 22, 7627, https://doi.org/10.1021/ja00777a003 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Keesee and Castleman, 1986
Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy 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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