Ethanol, 2,2,2-trifluoro-

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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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
MS - José A. Martinho Simões

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Individual Reactions

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

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

Quantity Value Units Method Reference Comment
Δr164. ± 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
Δr112.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
Δr130. ± 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+ • Ethanol, 2,2,2-trifluoro-)

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

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

Quantity Value Units Method Reference Comment
Δr133.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
Δr121.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
Δr97.1kJ/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- • Ethanol, 2,2,2-trifluoro-)

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

Quantity Value Units Method Reference Comment
Δr100.4 ± 3.3kJ/molTDAsLarson, Szulejko, et al., 1988gas phase; B,M
Δr103. ± 15.kJ/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Δr130.J/mol*KPHPMSLarson, Szulejko, et al., 1988gas phase; M
Δr109.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
Δr63.18 ± 0.84kJ/molTDAsLarson, Szulejko, et al., 1988gas phase; B
Δr68.6 ± 9.6kJ/molIMRELarson and McMahon, 1987gas phase; B,M

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

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

Quantity Value Units Method Reference Comment
Δr100. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Δr105.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
Δr69.0 ± 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
Δr1513. ± 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
Δr1482. ± 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- • Ethanol, 2,2,2-trifluoro-)

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

Quantity Value Units Method Reference Comment
Δr112.1 ± 2.1kJ/molTDAsSieck and Meot-ner, 1989gas phase; B,M
Quantity Value Units Method Reference Comment
Δr94.6J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr84.1 ± 6.3kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

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

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

Quantity Value Units Method Reference Comment
Δr86.2 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr102.J/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr55.6 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase; B

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

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

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

Quantity Value Units Method Reference Comment
Δr79.9kJ/molPHPMSMeot-Ner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Δr119.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
Δr87.86 ± 0.84kJ/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Δr56.5 ± 2.5kJ/molTDAsSieck and Meot-ner, 1989gas phase; B

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

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

Quantity Value Units Method Reference Comment
Δr87.9kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Δr105.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
Δr128. ± 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
Δr-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
Δr-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
Δr-199.6kJ/molRSCHolm, 1983solvent: Diethyl ether; MS

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

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

Quantity Value Units Method Reference Comment
Δr84.1 ± 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

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