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Phenol, pentafluoro-

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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

Quantity Value Units Method Reference Comment
Deltafgas-228.8 ± 0.48kcal/molCcrCox, Gundry, et al., 1969 

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafsolid-244.86 ± 0.48kcal/molCcrCox, Gundry, et al., 1969ALS
Quantity Value Units Method Reference Comment
Deltacsolid-567.57 ± 0.48kcal/molCcrCox, Gundry, et al., 1969ALS
Quantity Value Units Method Reference Comment
solid,1 bar58.040cal/mol*KN/APaukov, Lavrent'eva, et al., 1969crystaline, I phase; DH
solid,1 bar54.28cal/mol*KN/AAndon, Counsell, et al., 1968crystaline, I phase; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
62.299298.15Paukov, Lavrent'eva, et al., 1969crystaline, I phase; T = 12 to 329 K.; DH
48.11298.15Andon, Counsell, et al., 1968crystaline, I phase; T = 12 to 377 K.; DH

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

Bromine anion + Phenol, pentafluoro- = (Bromine anion bullet Phenol, pentafluoro-)

By formula: Br- + C6HF5O = (Br- bullet C6HF5O)

Quantity Value Units Method Reference Comment
Deltar25.6 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar23.cal/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar15.9 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
15.9423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

C6F5O- + Hydrogen cation = Phenol, pentafluoro-

By formula: C6F5O- + H+ = C6HF5O

Quantity Value Units Method Reference Comment
Deltar328.0 ± 2.2kcal/molG+TSKoppel, Taft, et al., 1994gas phase; B
Deltar<389.5 ± 2.7kcal/molAcidBriscese and Riveros, 1975gas phase; HO- + C6F6 -> , acidity probably ca. 320 kcal; B
Quantity Value Units Method Reference Comment
Deltar320.8 ± 2.0kcal/molIMREKoppel, Taft, et al., 1994gas phase; B

C20H32O2Zr (solution) + Phenol, pentafluoro- (solution) = C26H31F5O2Zr (solution) + Water (solution)

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

Quantity Value Units Method Reference Comment
Deltar-8.01 ± 0.31kcal/molRSCSchock and Marks, 1988solvent: Toluene; MS

C26H31F5O2Zr (solution) + Phenol, pentafluoro- (solution) = C32H30F10O2Zr (solution) + Water (solution)

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

Quantity Value Units Method Reference Comment
Deltar-4.59 ± 0.41kcal/molRSCSchock and Marks, 1988solvent: Toluene; MS

C20H32Zr (solution) + Phenol, pentafluoro- (solution) = C26H31F5OZr (solution) + Hydrogen (g)

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

Quantity Value Units Method Reference Comment
Deltar-34.20 ± 0.31kcal/molRSCSchock and Marks, 1988solvent: Toluene; MS

C26H31F5OZr (solution) + Phenol, pentafluoro- (solution) = C32H30F10O2Zr (solution) + Hydrogen (g)

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

Quantity Value Units Method Reference Comment
Deltar-24.69 ± 0.60kcal/molRSCSchock and Marks, 1988solvent: Toluene; MS

C13H24Zr (solution) + Phenol, pentafluoro- (solution) = C18H21F5OZr (solution) + Methane (g)

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

Quantity Value Units Method Reference Comment
Deltar-44.91 ± 0.50kcal/molRSCSchock and Marks, 1988solvent: Toluene; MS

C18H21F5OZr (solution) + Phenol, pentafluoro- (solution) = C23H18F10O2Zr (solution) + Methane (g)

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

Quantity Value Units Method Reference Comment
Deltar-41.80 ± 0.69kcal/molRSCSchock and Marks, 1988solvent: Toluene; MS

C13H24Hf (solution) + Phenol, pentafluoro- (solution) = C18H21F5HfO (solution) + Methane (g)

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

Quantity Value Units Method Reference Comment
Deltar-42.59 ± 0.31kcal/molRSCSchock and Marks, 1988solvent: Toluene; MS

C18H21F5HfO (solution) + Phenol, pentafluoro- (solution) = C23H18F10HfO2 (solution) + Methane (g)

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

Quantity Value Units Method Reference Comment
Deltar-41.11 ± 0.41kcal/molRSCSchock and Marks, 1988solvent: Toluene; MS

C5H11BrMg (solution) + Phenol, pentafluoro- (solution) = C6BrF5MgO (cr) + Pentane (solution)

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

Quantity Value Units Method Reference Comment
Deltar-55.90kcal/molRSCHolm, 1983solvent: Diethyl ether; MS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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]

Paukov, Lavrent'eva, et al., 1969
Paukov, I.E.; Lavrent'eva, M.N.; Anisimov, M.P., Heat capacity, phase transitions, entropy, and enthalpy of pentafluorophenol at low temperatures, Zhur. Fiz. Khim., 1969, 43, 785-787. [all data]

Andon, Counsell, et al., 1968
Andon, R.J.L.; Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F., Thermodynamic properties of fluorine compounds. Part VII. Heat capacity and entropy of pentafluorochelorobenzene and pentafluorophenol, J. Chem. Soc. A, 1968, 2357-2361. [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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References