Ethanol, 2,2,2-trifluoro-

• Formula: C₂H₃F₃O
• Molecular weight: 100.0398
• IUPAC Standard InChI: InChI=1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2 Copy

  
• IUPAC Standard InChIKey: RHQDFWAXVIIEBN-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-89-8
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: β,β,β-Trifluoroethyl alcohol; Fluorinol 85; 2,2,2-Trifluoroethanol; 2,2,2-Trifluoroethyl alcohol; CF3CH2OH; Perfluoro-1,1-dihydroethanol; TFE; NSC 451; 1,1H-perfluoroethanol
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Ion clustering data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

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

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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

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

 +  = ( • )

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

C₂H₄F₃O⁺ +  = (C₂H₄F₃O⁺ • )

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

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

CN^- +  = (CN^- • )

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

 +  = ( • )

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

C₂H₂F₃O^- +  =

By formula: C₂H₂F₃O^- + H⁺ = C₂H₃F₃O

HS^- +  = (HS^- • )

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

 +  = ( • )

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

CH₆N⁺ +  = (CH₆N⁺ • )

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

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

 +  = C₈H₈F₃OS^-

By formula: C₆H₅S^- + C₂H₃F₃O = C₈H₈F₃OS^-

 +  = ( • )

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

 +  = C₂H₂D₃F₄O^-

By formula: F^- + C₂H₃F₃O = C₂H₂D₃F₄O^-

C₂₀H₃₂Zr (solution) +  (solution) = C₂₂H₃₃F₃OZr (solution) +  (g)

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

C₂₂H₃₃F₃OZr (solution) +  (solution) = C₂₄H₃₄F₆O₂Zr (solution) +  (g)

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

C₅H₁₁BrMg (solution) +  (solution) = C₂H₂BrF₃MgO (solution) +  (solution)

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

 +  = ( • )

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

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

De-protonation reactions

C₂H₂F₃O^- +  =

By formula: C₂H₂F₃O^- + H⁺ = C₂H₃F₃O

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); BAIRD (GRATING); 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]

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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]

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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]

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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]

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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
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Meot-ner, 1988
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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]

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Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

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Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

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Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technical_series₁997-01-01₁.pdf. [all data]

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Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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