Phenol, 3-fluoro-

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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

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

C6H4FO- + Hydrogen cation = Phenol, 3-fluoro-

By formula: C6H4FO- + H+ = C6H5FO

Quantity Value Units Method Reference Comment
Δr1438. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1438. ± 12.kJ/molD-EAHernandez-Gill, Wentworth, et al., 1984gas phase; B
Δr1441. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1409. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1409. ± 12.kJ/molH-TSHernandez-Gill, Wentworth, et al., 1984gas phase; B
Δr1413. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Iodide + Phenol, 3-fluoro- = (Iodide • Phenol, 3-fluoro-)

By formula: I- + C6H5FO = (I- • C6H5FO)

Quantity Value Units Method Reference Comment
Δr81.2 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr88.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr43.9 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
44.8423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

Bromine anion + Phenol, 3-fluoro- = (Bromine anion • Phenol, 3-fluoro-)

By formula: Br- + C6H5FO = (Br- • C6H5FO)

Quantity Value Units Method Reference Comment
Δr97.9 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr57.3 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
57.3423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

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.

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Hernandez-Gill, Wentworth, et al., 1984
Hernandez-Gill, N.; Wentworth, W.E.; Chen, E.C.M., Electron affinities of fluorinated phenoxy radicals, J. Phys. Chem., 1984, 88, 6181. [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [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]


Notes

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