Phenol, pentafluoro-

• Formula: C₆HF₅O
• Molecular weight: 184.0636
• IUPAC Standard InChI: InChI=1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H Copy

  
• IUPAC Standard InChIKey: XBNGYFFABRKICK-UHFFFAOYSA-N Copy
• CAS Registry Number: 771-61-9
• 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: Pentafluorophenol; C6F5OH; 2,3,4,5,6-Pentafluorophenol
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
• Options:
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Gas 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

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: Br^- + C₆HF₅O = (Br^- • C₆HF₅O)

Free energy of reaction

C₆F₅O^- +  =

By formula: C₆F₅O^- + H⁺ = C₆HF₅O

C₂₀H₃₂O₂Zr (solution) +  (solution) = C₂₆H₃₁F₅O₂Zr (solution) +  (solution)

By formula: C₂₀H₃₂O₂Zr (solution) + C₆HF₅O (solution) = C₂₆H₃₁F₅O₂Zr (solution) + H₂O (solution)

C₂₆H₃₁F₅O₂Zr (solution) +  (solution) = C₃₂H₃₀F₁₀O₂Zr (solution) +  (solution)

By formula: C₂₆H₃₁F₅O₂Zr (solution) + C₆HF₅O (solution) = C₃₂H₃₀F₁₀O₂Zr (solution) + H₂O (solution)

C₂₀H₃₂Zr (solution) +  (solution) = C₂₆H₃₁F₅OZr (solution) +  (g)

By formula: C₂₀H₃₂Zr (solution) + C₆HF₅O (solution) = C₂₆H₃₁F₅OZr (solution) + H₂ (g)

C₂₆H₃₁F₅OZr (solution) +  (solution) = C₃₂H₃₀F₁₀O₂Zr (solution) +  (g)

By formula: C₂₆H₃₁F₅OZr (solution) + C₆HF₅O (solution) = C₃₂H₃₀F₁₀O₂Zr (solution) + H₂ (g)

C₁₃H₂₄Zr (solution) +  (solution) = C₁₈H₂₁F₅OZr (solution) +  (g)

By formula: C₁₃H₂₄Zr (solution) + C₆HF₅O (solution) = C₁₈H₂₁F₅OZr (solution) + CH₄ (g)

C₁₈H₂₁F₅OZr (solution) +  (solution) = C₂₃H₁₈F₁₀O₂Zr (solution) +  (g)

By formula: C₁₈H₂₁F₅OZr (solution) + C₆HF₅O (solution) = C₂₃H₁₈F₁₀O₂Zr (solution) + CH₄ (g)

C₁₃H₂₄Hf (solution) +  (solution) = C₁₈H₂₁F₅HfO (solution) +  (g)

By formula: C₁₃H₂₄Hf (solution) + C₆HF₅O (solution) = C₁₈H₂₁F₅HfO (solution) + CH₄ (g)

C₁₈H₂₁F₅HfO (solution) +  (solution) = C₂₃H₁₈F₁₀HfO₂ (solution) +  (g)

By formula: C₁₈H₂₁F₅HfO (solution) + C₆HF₅O (solution) = C₂₃H₁₈F₁₀HfO₂ (solution) + CH₄ (g)

C₅H₁₁BrMg (solution) +  (solution) = C₆BrF₅MgO (cr) +  (solution)

By formula: C₅H₁₁BrMg (solution) + C₆HF₅O (solution) = C₆BrF₅MgO (cr) + C₅H₁₂ (solution)

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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₆F₅O^- +  =

By formula: C₆F₅O^- + H⁺ = C₆HF₅O

Ion clustering 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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: Br^- + C₆HF₅O = (Br^- • C₆HF₅O)

Free energy of reaction

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-400 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 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

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

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

Cox, Gundry, et al., 1969
Cox, J.D.; Gundry, H.A.; Harrop, D.; Head, A.J., Thermodynamic properties of fluorine compounds. 9. Enthalpies of formation of some compounds containing the pentafluorophenyl group, J. Chem. Thermodyn., 1969, 1, 77-87. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [all data]

Koppel, Taft, et al., 1994
Koppel, I.A.; Taft, R.W.; Anvia, F.; Zhu, S.Z.; Hu, L.Q.; Sung, K.S.; Desmarteau, D.D.; Yagupolskii, L.M., The Gas-Phase Acidities of Very Strong Neutral Bronsted Acids, J. Am. Chem. Soc., 1994, 116, 7, 3047, https://doi.org/10.1021/ja00086a038 . [all data]

Briscese and Riveros, 1975
Briscese, S.M.J.; Riveros, J.M., Gas phase nucleophilic reactions of aromatic systems, J. Am. Chem. Soc., 1975, 97, 230. [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]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]

Maier, Marthaler, et al., 1980
Maier, J.P.; Marthaler, O.; Mohraz, M., Emission spectra of the cations of some fluorosubstituted phenols in the gaseous phase, J. Electron Spectrosc. Relat. Phenom., 1980, 19, 11. [all data]

(editor), 1967
(editor), Koptyug V.A., Atlas of Spectra of Aromatic and Heterocyclic Compounds, 1967, 1, 127. [all data]

Notes

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• Symbols used in this document:
  

  T	Temperature
  ΔfH°gas	Enthalpy of formation of gas 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

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