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
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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

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

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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões

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

C₂H₂F₃O₂⁺ +  = (C₂H₂F₃O₂⁺ • )

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

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

 +  =

By formula: C₂F₃O₂^- + H⁺ = C₂HF₃O₂

 +  =  + 

By formula: C₄F₆O₃ + C₅H₁₀O = C₇H₉F₃O₂ + C₂HF₃O₂

 +  =

By formula: C₇H₁₀ + C₂HF₃O₂ = C₉H₁₁F₃O₂

 +  =

By formula: C₇H₁₂ + C₂HF₃O₂ = C₉H₁₃F₃O₃

 +  =

By formula: C₆H₁₀ + C₂HF₃O₂ = C₈H₁₁F₃O₂

 +  =

By formula: C₅H₈ + C₂HF₃O₂ = C₇H₉F₃O₂

 +  =

By formula: C₇H₁₂ + C₂HF₃O₂ = C₉H₁₃F₃O₃

C₁₄H₁₀F₆MoO₄ (cr) + 2( • 4.40) (solution) = C₁₀H₁₀Cl₂Mo (cr) + 2 (l)

By formula: C₁₄H₁₀F₆MoO₄ (cr) + 2(HCl • 4.40H₂O) (solution) = C₁₀H₁₀Cl₂Mo (cr) + 2C₂HF₃O₂ (l)

C₁₄H₁₀F₆O₄Ti (cr) + 2( • 4.40) (solution) =  (cr) + 2 (l)

By formula: C₁₄H₁₀F₆O₄Ti (cr) + 2(HCl • 4.40H₂O) (solution) = C₁₀H₁₀Cl₂Ti (cr) + 2C₂HF₃O₂ (l)

C₁₄H₁₀F₆O₄W (cr) + 2( • 4.40) (solution) = C₁₀H₁₀Cl₂W (cr) + 2 (l)

By formula: C₁₄H₁₀F₆O₄W (cr) + 2(HCl • 4.40H₂O) (solution) = C₁₀H₁₀Cl₂W (cr) + 2C₂HF₃O₂ (l)

 +  =  + 

By formula: C₄F₆O₃ + C₇H₁₂O = C₉H₁₁F₃O₂ + C₂HF₃O₂

 +  =  + 

By formula: C₆H₁₂O + C₄F₆O₃ = C₈H₁₁F₃O₂ + C₂HF₃O₂

 +  =  + 

By formula: C₄F₆O₃ + C₅H₁₂O = C₇H₁₁F₃O₂ + C₂HF₃O₂

 +  =

By formula: C₂HF₃O₂ + C₆H₁₂ = C₈H₁₃F₃O₂

 +  =

By formula: C₂HF₃O₂ + C₆H₁₂ = C₈H₁₃F₃O₂

 +  =

By formula: C₆H₁₂ + C₂HF₃O₂ = C₈H₁₃F₃O₂

 +  =

By formula: C₆H₁₂ + C₂HF₃O₂ = C₈H₁₃F₃O₂

 +  =

By formula: C₆H₁₂ + C₂HF₃O₂ = C₈H₁₃F₃O₂

 +  =

By formula: C₆H₁₂ + C₂HF₃O₂ = C₈H₁₃F₃O₂

 +  =

By formula: C₅H₁₀ + C₂HF₃O₂ = C₇H₁₁F₃O₂

 +  =

By formula: C₅H₁₀ + C₂HF₃O₂ = C₇H₁₁F₃O₂

 +  =

By formula: C₂HF₃O₂ + C₆H₁₂ = C₈H₁₃F₃O₂

C₅H₁₁BrMg (solution) +  (solution) = C₂BrF₃MgO₂ (solution) +  (solution)

By formula: C₅H₁₁BrMg (solution) + C₂HF₃O₂ (solution) = C₂BrF₃MgO₂ (solution) + C₅H₁₂ (solution)

 +  =  + 

By formula: C₄F₆O₃ + C₆H₁₄O = C₂HF₃O₂ + C₈H₁₃F₃O₂

 +  =  + 

By formula: C₄F₆O₃ + C₆H₁₄O = C₂HF₃O₂ + C₈H₁₃F₃O₂

 +  = 2

By formula: C₄F₆O₃ + H₂O = 2C₂HF₃O₂

 +  = C₂F₃NO₄ + 

By formula: C₄F₆O₃ + HNO₃ = C₂F₃NO₄ + C₂HF₃O₂

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

References

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

Guthrie, 1976
Guthrie, J.P., Thermodynamics of ester and orthoester formation from trifluoroacetic acid, Can. J. Chem., 1976, 54, 202-209. [all data]

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]

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]

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]

Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A., Enthalpies of hydration of alkenes. 3. Cycloalkenes, J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]

Calado, Dias, et al., 1981
Calado, J.C.G.; Dias, A.R.; Salema, M.S.; Martinho Simões, J.A., J. Chem. Soc., Dalton Trans., 1981, 1174.. [all data]

Calhorda, Carrondo, et al., 1986
Calhorda, M.J.; Carrondo, M.A.A.F.C.T.; Dias, A.R.; Domingos, A.M.T.S.; Martinho Simões, J.A.; Teixeira, C., Organometallics, 1986, 5, 660. [all data]

Wiberg and Hao, 1991
Wiberg, K.B.; Hao, S., Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols, J. Org. Chem., 1991, 56, 5108-5110. [all data]

Wiberg and Wasserman, 1981
Wiberg, K.B.; Wasserman, D.J., Enthalpies of hydration of alkenes. 1. The n-hexenes, J. Am. Chem. Soc., 1981, 103, 6563-6566. [all data]

Holm, 1983
Holm, T., Acta Chem. Scand. B, 1983, 37, 797. [all data]

Tsvetkov, Shmakov, et al., 1989
Tsvetkov, V.G.; Shmakov, V.A.; Sopin, V.F.; Ivanov, A.V.; Ikonnikov, A.A.; Marchenko, G.N., Enthalpies of reaction of nitric acid with acetic and trifluoroacetic anhydrides, J. Gen. Chem. USSR, 1989, 59, 1220-1222. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References

• Symbols used in this document:
  

  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas 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
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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