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Ethanol, 2,2,2-trifluoro-

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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: H.Y. Afeefy, J.F. Liebman, and S.E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid-932.57 ± 0.79kJ/molCcrKolesov, Ivanov, et al., 1971Corrected for CODATA value of «DELTA»fH; Correction of Kolesov, Zenkov, et al., 1965
Quantity Value Units Method Reference Comment
Deltacliquid-821.53 ± 0.79kJ/molCcrKolesov, Ivanov, et al., 1971Corrected for CODATA value of «DELTA»fH; Correction of Kolesov, Zenkov, et al., 1965

Phase change 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:
BS - R.L. Brown and S.E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, M. Frenkel director
ALS - H.Y. Afeefy, J.F. Liebman, and S.E. Stein
AC - W.E. Acree, Jr., J.S. Chickos

Quantity Value Units Method Reference Comment
Tboil348. ± 3.KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus229.65KN/AKobayashi and Nagashima, 1985Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Tc498.57KN/ABier, Tuerk, et al., 1990Uncertainty assigned by TRC = 0.1 K; TRC
Quantity Value Units Method Reference Comment
Pc48.25barN/ABier, Tuerk, et al., 1990Uncertainty assigned by TRC = 0.15 bar; TRC
Quantity Value Units Method Reference Comment
Deltavap43.97kJ/molVRochester and Symonds, 1973ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
45.9289.AStephenson and Malanowski, 1987Based on data from 276. - 302. K.; AC
44.0313.AStephenson and Malanowski, 1987Based on data from 298. - 328. K. See also Dykyj, 1970.; AC
41.5313.MMRochester and Symonds, 1973Based on data from 298. - 328. K.; AC
44.5285.MMMeeks and Goldfarb, 1967Based on data from 273. - 298. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
272.8 - 298.63.56946855.921-111.932Meeks and Goldfarb, 1967, 2Coefficents calculated by NIST from author's data.

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 - J.E. Bartmess
M - M. M. Meot-Ner (Mautner) and S. G. Lias
MS - J.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

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spec Data Center, S.E. Stein, director


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

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

Data compiled by: NIST Mass Spec Data Center, S.E. Stein, director

Spectrum

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 118716

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes

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

Kolesov, Ivanov, et al., 1971
Kolesov, V.P.; Ivanov, L.S.; Skuratov, S.M., The standard enthalpy of formation of 2,2,2-trifluoroethanol, Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 303-305. [all data]

Kolesov, Zenkov, et al., 1965
Kolesov, V.P.; Zenkov, I.D.; Skuratov, S.M., Standard enthalpy of formation of 2,2,2-trifluoroethanol, Russ. J. Phys. Chem. (Engl. Transl.), 1965, 39, 1320-1322. [all data]

Kobayashi and Nagashima, 1985
Kobayashi, K.; Nagashima, A., Measurement of the Viscosity of Trifluoroethanol and Its Aqueous Solutions under High Pressure, Bull. JSME, 1985, 28, 1453. [all data]

Bier, Tuerk, et al., 1990
Bier, K.; Tuerk, M.; Zhai, J., Vapor. press. of trifluoroethanol in Int. Inst. Ref., Comm. B1, Proc. Meet., Herzlia, Israel, 129-39, 1990. [all data]

Rochester and Symonds, 1973
Rochester, C.H.; Symonds, J.R., Thermodynamic studies of fluoroalchols Part 1.-Vapour pressures and enthalpies of vaporization, J. Chem. Soc. Faraday Trans. 1, 1973, 69, 1267. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Dykyj, 1970
Dykyj, J., Petrochemica, 1970, 10, 2, 51. [all data]

Meeks and Goldfarb, 1967
Meeks, Alan C.; Goldfarb, Ivan J., Vapor pressure of fluoroalcohols, J. Chem. Eng. Data, 1967, 12, 2, 196-196, https://doi.org/10.1021/je60033a010 . [all data]

Meeks and Goldfarb, 1967, 2
Meeks, A.C.; Goldfarb, I.J., Vapor Pressure of Fluoroalcohols, J. Chem. Eng. Data, 1967, 12, 2, 196, https://doi.org/10.1021/je60033a010 . [all data]

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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References