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Trifluoroacetic acid

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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+ + Trifluoroacetic acid = (C2H2F3O2+ bullet Trifluoroacetic acid)

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

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

Quantity Value Units Method Reference Comment
Deltar29.3kcal/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
Deltar28.5cal/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
Deltar20.8kcal/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
Deltar323.8 ± 2.9kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Deltar322.8 ± 2.9kcal/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale; B
Deltar322.8 ± 4.1kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar317.4 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Deltar316.4 ± 2.0kcal/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale; B
Deltar316.3 ± 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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-8.74 ± 0.21kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis; ALS

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

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

Quantity Value Units Method Reference Comment
Deltar13.9 ± 0.60kcal/molRSCCalado, Dias, et al., 1981Please also see Calhorda, Carrondo, et al., 1986.; MS

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

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

Quantity Value Units Method Reference Comment
Deltar9.03 ± 0.55kcal/molRSCCalado, Dias, et al., 1981Please also see Calhorda, Carrondo, et al., 1986.; MS

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

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

Quantity Value Units Method Reference Comment
Deltar7.62 ± 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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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
Deltar-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

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