Trifluoroacetic acid

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.


Reaction thermochemistry data

Go To: Top, 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:
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+ + Trifluoroacetic acid = (C2H2F3O2+ • Trifluoroacetic acid)

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

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

Quantity Value Units Method Reference Comment
Δr29.3kcal/molICRLarson and McMahon, 1982gas phase; switching reaction(H3O+)H2O, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
Δr28.5cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction(H3O+)H2O, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
Δr20.8kcal/molICRLarson and McMahon, 1982gas phase; switching reaction(H3O+)H2O, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

CF3CO2 anion + Hydrogen cation = Trifluoroacetic acid

By formula: C2F3O2- + H+ = C2HF3O2

Quantity Value Units Method Reference Comment
Δr323.8 ± 2.9kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr322.8 ± 2.9kcal/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale; B
Δr322.8 ± 4.1kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr317.4 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr316.4 ± 2.0kcal/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale; B
Δr316.3 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

Acetic acid, trifluoro-, anhydride + Cyclopentanol = Trifluoroacetic acid, cyclopentyl ester + Trifluoroacetic acid

By formula: C4F6O3 + C5H10O = C7H9F3O2 + C2HF3O2

Quantity Value Units Method Reference Comment
Δr-22.219 ± 0.056kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroactic acid; Trifluoroacetolysis; ALS

2-Norbornene + Trifluoroacetic acid = exo-Norborneol, trifluoroacetate

By formula: C7H10 + C2HF3O2 = C9H11F3O2

Quantity Value Units Method Reference Comment
Δr-15.333 ± 0.055kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis; ALS

Cyclohexane, methylene- + Trifluoroacetic acid = Acetic acid, trifluoro-, 1-methyl cyclohexyl ester

By formula: C7H12 + C2HF3O2 = C9H13F3O3

Quantity Value Units Method Reference Comment
Δr-10.710 ± 0.024kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis; ALS

Cyclohexene + Trifluoroacetic acid = Acetic acid, trifluoro-, cyclohexyl ester

By formula: C6H10 + C2HF3O2 = C8H11F3O2

Quantity Value Units Method Reference Comment
Δr-10.36 ± 0.03kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Triflouroacetolysis; ALS

Cyclopentene + Trifluoroacetic acid = Trifluoroacetic acid, cyclopentyl ester

By formula: C5H8 + C2HF3O2 = C7H9F3O2

Quantity Value Units Method Reference Comment
Δr-9.167 ± 0.044kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis; ALS

Cyclohexene, 1-methyl- + Trifluoroacetic acid = Acetic acid, trifluoro-, 1-methyl cyclohexyl ester

By formula: C7H12 + C2HF3O2 = C9H13F3O3

Quantity Value Units Method Reference Comment
Δr-8.74 ± 0.21kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis; ALS

C14H10F6MoO4 (cr) + 2(Hydrogen chloride • 4.40Water) (solution) = C10H10Cl2Mo (cr) + 2Trifluoroacetic acid (l)

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

Quantity Value Units Method Reference Comment
Δr13.9 ± 0.60kcal/molRSCCalado, Dias, et al., 1981Please also see Calhorda, Carrondo, et al., 1986.; MS

C14H10F6O4Ti (cr) + 2(Hydrogen chloride • 4.40Water) (solution) = Titanocene dichloride (cr) + 2Trifluoroacetic acid (l)

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

Quantity Value Units Method Reference Comment
Δr9.03 ± 0.55kcal/molRSCCalado, Dias, et al., 1981Please also see Calhorda, Carrondo, et al., 1986.; MS

C14H10F6O4W (cr) + 2(Hydrogen chloride • 4.40Water) (solution) = C10H10Cl2W (cr) + 2Trifluoroacetic acid (l)

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

Quantity Value Units Method Reference Comment
Δr7.62 ± 0.45kcal/molRSCCalado, Dias, et al., 1981Please also see Calhorda, Carrondo, et al., 1986.; MS

Acetic acid, trifluoro-, anhydride + exo-Norbornyl alcohol = exo-Norborneol, trifluoroacetate + Trifluoroacetic acid

By formula: C4F6O3 + C7H12O = C9H11F3O2 + C2HF3O2

Quantity Value Units Method Reference Comment
Δr-21.771 ± 0.034kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; Trifluoroacetolysis; ALS

Cyclohexanol + Acetic acid, trifluoro-, anhydride = Acetic acid, trifluoro-, cyclohexyl ester + Trifluoroacetic acid

By formula: C6H12O + C4F6O3 = C8H11F3O2 + C2HF3O2

Quantity Value Units Method Reference Comment
Δr-21.524 ± 0.037kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; Trifluoroacetolysis; ALS

Acetic acid, trifluoro-, anhydride + Amylene hydrate = Acetic acid, trifluoro-, 2,2-dimethylpropyl ester + Trifluoroacetic acid

By formula: C4F6O3 + C5H12O = C7H11F3O2 + C2HF3O2

Quantity Value Units Method Reference Comment
Δr-21.16 ± 0.02kcal/molCmWiberg and Hao, 1991liquid phase; Trifuoroacetolysis; ALS

Trifluoroacetic acid + 3-Hexene, (Z)- = Acetic acid, 2,2,2-trifluoro-, 1-methylpentyl ester

By formula: C2HF3O2 + C6H12 = C8H13F3O2

Quantity Value Units Method Reference Comment
Δr-10.704 ± 0.032kcal/molEqkWiberg and Wasserman, 1981liquid phase; Trifluoroacetolysis; ALS

Trifluoroacetic acid + 2-Hexene, (Z)- = Acetic acid, 2,2,2-trifluoro-, 1-methylpentyl ester

By formula: C2HF3O2 + C6H12 = C8H13F3O2

Quantity Value Units Method Reference Comment
Δr-10.220 ± 0.030kcal/molEqkWiberg and Wasserman, 1981liquid phase; Trifluoroacetolysis; ALS

3-Hexene, (E)- + Trifluoroacetic acid = Acetic acid, 2,2,2-trifluoro-, 1-methylpentyl ester

By formula: C6H12 + C2HF3O2 = C8H13F3O2

Quantity Value Units Method Reference Comment
Δr-9.775 ± 0.031kcal/molEqkWiberg and Wasserman, 1981liquid phase; Trifluoroacetolysis; ALS

2-Hexene, (E)- + Trifluoroacetic acid = Acetic acid, 2,2,2-trifluoro-, 1-methylpentyl ester

By formula: C6H12 + C2HF3O2 = C8H13F3O2

Quantity Value Units Method Reference Comment
Δr-9.492 ± 0.032kcal/molEqkWiberg and Wasserman, 1981liquid phase; Trifluoroacetolysis; ALS

2-Pentene, 3-methyl-, (E)- + Trifluoroacetic acid = Acetic acid, trifluoro-, 1,2-dimethylbutyl ester, (R*,S*)-(+/-)-

By formula: C6H12 + C2HF3O2 = C8H13F3O2

Quantity Value Units Method Reference Comment
Δr-8.79 ± 0.06kcal/molCmWiberg and Hao, 1991liquid phase; Trifluoroacetolysis; ALS

1-Hexene + Trifluoroacetic acid = Acetic acid, 2,2,2-trifluoro-, 1-methylpentyl ester

By formula: C6H12 + C2HF3O2 = C8H13F3O2

Quantity Value Units Method Reference Comment
Δr-12.07 ± 0.03kcal/molEqkWiberg and Wasserman, 1981liquid phase; Trifluoroacetolysis; ALS

2-Methyl-1-butene + Trifluoroacetic acid = Acetic acid, trifluoro-, 2,2-dimethylpropyl ester

By formula: C5H10 + C2HF3O2 = C7H11F3O2

Quantity Value Units Method Reference Comment
Δr-10.93 ± 0.04kcal/molCmWiberg and Hao, 1991liquid phase; Trifuoroacetolysis; ALS

2-Butene, 2-methyl- + Trifluoroacetic acid = Acetic acid, trifluoro-, 2,2-dimethylpropyl ester

By formula: C5H10 + C2HF3O2 = C7H11F3O2

Quantity Value Units Method Reference Comment
Δr-9.11 ± 0.04kcal/molCmWiberg and Hao, 1991liquid phase; Trifluoroacetolysis; ALS

Trifluoroacetic acid + 2-Pentene, 3-methyl-, (Z)- = Acetic acid, trifluoro-, 1,2-dimethylbutyl ester, (R*,S*)-(+/-)-

By formula: C2HF3O2 + C6H12 = C8H13F3O2

Quantity Value Units Method Reference Comment
Δr-9.01 ± 0.02kcal/molCmWiberg and Hao, 1991liquid phase; Trifuoroacetolysis; ALS

C5H11BrMg (solution) + Trifluoroacetic acid (solution) = C2BrF3MgO2 (solution) + Pentane (solution)

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

Quantity Value Units Method Reference Comment
Δr-65.39kcal/molRSCHolm, 1983solvent: Diethyl ether; MS

Acetic acid, trifluoro-, anhydride + 2-Hexanol = Trifluoroacetic acid + Acetic acid, 2,2,2-trifluoro-, 1-methylpentyl ester

By formula: C4F6O3 + C6H14O = C2HF3O2 + C8H13F3O2

Quantity Value Units Method Reference Comment
Δr-21.35 ± 0.01kcal/molCmWiberg and Wasserman, 1981liquid phase; ALS

Acetic acid, trifluoro-, anhydride + 3-Hexanol = Trifluoroacetic acid + Hexan-3-yl trifluoroacetate

By formula: C4F6O3 + C6H14O = C2HF3O2 + C8H13F3O2

Quantity Value Units Method Reference Comment
Δr-22.15 ± 0.01kcal/molCmWiberg and Wasserman, 1981liquid phase; ALS

Acetic acid, trifluoro-, anhydride + Water = 2Trifluoroacetic acid

By formula: C4F6O3 + H2O = 2C2HF3O2

Quantity Value Units Method Reference Comment
Δr-18.01 ± 0.01kcal/molCmWiberg and Wasserman, 1981liquid phase; ALS

Acetic acid, trifluoro-, anhydride + Nitric acid = C2F3NO4 + Trifluoroacetic acid

By formula: C4F6O3 + HNO3 = C2F3NO4 + C2HF3O2

Quantity Value Units Method Reference Comment
Δr-6.60kcal/molCmTsvetkov, Shmakov, et al., 1989liquid phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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

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, Reaction thermochemistry data, References