mF-phenoxide anion


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 by: John E. Bartmess

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Individual Reactions

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

By formula: C6H4FO- + H+ = C6H5FO

Quantity Value Units Method Reference Comment
Δr343.6 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr343.6 ± 2.8kcal/molD-EAHernandez-Gill, Wentworth, et al., 1984gas phase
Δr344.5 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr336.8 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr336.7 ± 2.9kcal/molH-TSHernandez-Gill, Wentworth, et al., 1984gas phase
Δr337.6 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

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 by: John E. Bartmess

Electron affinity of neutral species

EAneutral (eV) Method Reference Comment
2.61 ± 0.12D-EAFujio, McIver, et al., 1981value altered from reference due to change in acidity scale
2.611 ± 0.087ECDHernandez-Gill, Wentworth, et al., 1984 

Protonation reactions

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

By formula: C6H4FO- + H+ = C6H5FO

Quantity Value Units Method Reference Comment
Δr343.6 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr343.6 ± 2.8kcal/molD-EAHernandez-Gill, Wentworth, et al., 1984gas phase
Δr344.5 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr336.8 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr336.7 ± 2.9kcal/molH-TSHernandez-Gill, Wentworth, et al., 1984gas phase
Δr337.6 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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]


Notes

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