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Phenol, pentafluoro-

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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

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

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

Quantity Value Units Method Reference Comment
Deltar107. ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar96.J/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
Deltar66.5 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
66.5423.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
Deltar1372. ± 9.2kJ/molG+TSKoppel, Taft, et al., 1994gas phase; B
Deltar<1630. ± 11.kJ/molAcidBriscese and Riveros, 1975gas phase; HO- + C6F6 -> , acidity probably ca. 320 kcal; B
Quantity Value Units Method Reference Comment
Deltar1342. ± 8.4kJ/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-33.5 ± 1.3kJ/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-19.2 ± 1.7kJ/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-143.1 ± 1.3kJ/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-103.3 ± 2.5kJ/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-187.9 ± 2.1kJ/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-174.9 ± 2.9kJ/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-178.2 ± 1.3kJ/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-172.0 ± 1.7kJ/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-233.9kJ/molRSCHolm, 1983solvent: Diethyl ether; MS

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.

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

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