Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

Ethanol, 2,2,2-trifluoro-

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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

Fluorine anion + Ethanol, 2,2,2-trifluoro- = (Fluorine anion bullet Ethanol, 2,2,2-trifluoro-)

By formula: F- + C2H3F3O = (F- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar164. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B,M
Quantity Value Units Method Reference Comment
Deltar112.J/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Deltar130. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B,M

C2H4F3O+ + Ethanol, 2,2,2-trifluoro- = (C2H4F3O+ bullet Ethanol, 2,2,2-trifluoro-)

By formula: C2H4F3O+ + C2H3F3O = (C2H4F3O+ bullet C2H3F3O)

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

Quantity Value Units Method Reference Comment
Deltar133.kJ/molICRLarson and McMahon, 1982gas phase; switching reaction(H2O)2H+, 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
Deltar121.J/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction(H2O)2H+, 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
Deltar97.1kJ/molICRLarson and McMahon, 1982gas phase; switching reaction(H2O)2H+, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

CN- + Ethanol, 2,2,2-trifluoro- = (CN- bullet Ethanol, 2,2,2-trifluoro-)

By formula: CN- + C2H3F3O = (CN- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar100.4 ± 3.3kJ/molTDAsLarson, Szulejko, et al., 1988gas phase; B,M
Deltar103. ± 15.kJ/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar130.J/mol*KPHPMSLarson, Szulejko, et al., 1988gas phase; M
Deltar109.J/mol*KN/ALarson and McMahon, 1987gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M
Quantity Value Units Method Reference Comment
Deltar63.18 ± 0.84kJ/molTDAsLarson, Szulejko, et al., 1988gas phase; B
Deltar68.6 ± 9.6kJ/molIMRELarson and McMahon, 1987gas phase; B,M

Chlorine anion + Ethanol, 2,2,2-trifluoro- = (Chlorine anion bullet Ethanol, 2,2,2-trifluoro-)

By formula: Cl- + C2H3F3O = (Cl- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar100. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar105.J/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)CH3COOH, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Deltar69.0 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

C2H2F3O- + Hydrogen cation = Ethanol, 2,2,2-trifluoro-

By formula: C2H2F3O- + H+ = C2H3F3O

Quantity Value Units Method Reference Comment
Deltar1513. ± 10.kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1482. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

HS- + Ethanol, 2,2,2-trifluoro- = (HS- bullet Ethanol, 2,2,2-trifluoro-)

By formula: HS- + C2H3F3O = (HS- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar112.1 ± 2.1kJ/molTDAsSieck and Meot-ner, 1989gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar94.6J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar84.1 ± 6.3kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

cyclopentadienide anion + Ethanol, 2,2,2-trifluoro- = (cyclopentadienide anion bullet Ethanol, 2,2,2-trifluoro-)

By formula: C5H5- + C2H3F3O = (C5H5- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar86.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar102.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar55.6 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

CH6N+ + Ethanol, 2,2,2-trifluoro- = (CH6N+ bullet Ethanol, 2,2,2-trifluoro-)

By formula: CH6N+ + C2H3F3O = (CH6N+ bullet C2H3F3O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Deltar79.9kJ/molPHPMSMeot-Ner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar119.J/mol*KPHPMSMeot-Ner, 1984gas phase; M

thiophenoxide anion + Ethanol, 2,2,2-trifluoro- = C8H8F3OS-

By formula: C6H5S- + C2H3F3O = C8H8F3OS-

Quantity Value Units Method Reference Comment
Deltar87.86 ± 0.84kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar56.5 ± 2.5kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

thiophenoxide anion + Ethanol, 2,2,2-trifluoro- = (thiophenoxide anion bullet Ethanol, 2,2,2-trifluoro-)

By formula: C6H5S- + C2H3F3O = (C6H5S- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar87.9kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar105.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

Fluorine anion + Ethanol, 2,2,2-trifluoro- = C2H2D3F4O-

By formula: F- + C2H3F3O = C2H2D3F4O-

Quantity Value Units Method Reference Comment
Deltar128. ± 8.4kJ/molIMREWilkinson, Szulejko, et al., 1992gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B

C20H32Zr (solution) + Ethanol, 2,2,2-trifluoro- (solution) = C22H33F3OZr (solution) + Hydrogen (g)

By formula: C20H32Zr (solution) + C2H3F3O (solution) = C22H33F3OZr (solution) + H2 (g)

Quantity Value Units Method Reference Comment
Deltar-113.0 ± 2.1kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C22H33F3OZr (solution) + Ethanol, 2,2,2-trifluoro- (solution) = C24H34F6O2Zr (solution) + Hydrogen (g)

By formula: C22H33F3OZr (solution) + C2H3F3O (solution) = C24H34F6O2Zr (solution) + H2 (g)

Quantity Value Units Method Reference Comment
Deltar-84.1 ± 0.8kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C5H11BrMg (solution) + Ethanol, 2,2,2-trifluoro- (solution) = C2H2BrF3MgO (solution) + Pentane (solution)

By formula: C5H11BrMg (solution) + C2H3F3O (solution) = C2H2BrF3MgO (solution) + C5H12 (solution)

Quantity Value Units Method Reference Comment
Deltar-199.6kJ/molRSCHolm, 1983solvent: Diethyl ether; MS

Iodide + Ethanol, 2,2,2-trifluoro- = (Iodide bullet Ethanol, 2,2,2-trifluoro-)

By formula: I- + C2H3F3O = (I- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar84.1 ± 4.2kJ/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

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, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Bond dissociation energies of F2(-) and HF2(-). A gas-phase experimental and G2 theoretical study, J. Phys. Chem., 1995, 99, 7, 2002, https://doi.org/10.1021/j100007a034 . [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [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]

Larson, Szulejko, et al., 1988
Larson, J.W.; Szulejko, J.E.; McMahon, T.B., Gas Phase Lewis Acid-Base Interactions. An Experimental Determination of Cyanide Binding Energies From Ion Cyclotron Resonance and High-Pressure Mass Spectrometric Equilibrium Measurements., J. Am. Chem. Soc., 1988, 110, 23, 7604, https://doi.org/10.1021/ja00231a004 . [all data]

Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids, J. Am. Chem. Soc., 1987, 109, 6230. [all data]

Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P., Hydration of CN-, NO2-, NO3-, and HO- in the gas phase, Can. J. Chem., 1971, 49, 3308. [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Sieck and Meot-ner, 1989
Sieck, L.W.; Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. 8. RS-..HOR Bond Strengths. Correlation with Acidities., J. Phys. Chem., 1989, 93, 4, 1586, https://doi.org/10.1021/j100341a079 . [all data]

Meot-ner, 1988
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Wilkinson, Szulejko, et al., 1992
Wilkinson, F.E.; Szulejko, J.E.; Allison, C.E.; Mcmahon, T.B., Fourier Transform Ion Cyclotron Resonance Investigation of the Deuterium Isotope Effect on Gas Phase Ion/Molecule Hydrogen Bonding Interactions in Alcohol-Fluoride Adduct Ions, Int. J. Mass Spectrom., 1992, 117, 487-505, https://doi.org/10.1016/0168-1176(92)80110-M . [all data]

Schock and Marks, 1988
Schock, L.E.; Marks, T.J., J. Am. Chem. Soc., 1988, 110, 7701. [all data]

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

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]


Notes

Go To: Top, Reaction thermochemistry data, References