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1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)-2-propanol


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

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Individual Reactions

Fluorine anion + 1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)-2-propanol = (Fluorine anion bullet 1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)-2-propanol)

By formula: F- + C4HF9O = (F- bullet C4HF9O)

Quantity Value Units Method Reference Comment
Deltar236. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B
Quantity Value Units Method Reference Comment
Deltar200. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B

C4F9O- + Hydrogen cation = 1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)-2-propanol

By formula: C4F9O- + H+ = C4HF9O

Quantity Value Units Method Reference Comment
Deltar1387. ± 9.2kJ/molG+TSTaft, Koppel, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar1356. ± 8.4kJ/molIMRETaft, Koppel, et al., 1990gas phase; B
Deltar1352. ± 21.kJ/molIMRBKoppel, Pikver, et al., 1981gas phase; B
Deltar1345. ± 21.kJ/molIMRBClair and McMahon, 1980gas phase; B

Iodide + 1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)-2-propanol = (Iodide bullet 1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)-2-propanol)

By formula: I- + C4HF9O = (I- bullet C4HF9O)

Quantity Value Units Method Reference Comment
Deltar97.1 ± 4.2kJ/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,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.

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Bond dissociation energies of F2(-) and HF2(-). A gas-phase experimental and G2 theoretical study, J. Phys. Chem., 1995, 99, 7, 2002, https://doi.org/10.1021/j100007a034 . [all data]

Taft, Koppel, et al., 1990
Taft, R.W.; Koppel, I.J.; Topsom, R.D.; Anvia, F., Acidities of OH Compounds, including Alcohols, Phenols, Carboxylic Acids, and Mineral Acids, J. Am. Chem. Soc., 1990, 112, 6, 2047, https://doi.org/10.1021/ja00162a001 . [all data]

Koppel, Pikver, et al., 1981
Koppel, I.; Pikver, R.; Sugis, A.; Suurmaa, E.; Lippmaa, E., FTICR Study of Structure and Solvent Effects on Basicity of Some Anions in the Gas Phase, Org. Reac., 1981, 18, 3. [all data]

Clair and McMahon, 1980
Clair, R.L.; McMahon, T.B., An ion cyclotron resonance study of base-induced elimination reactions of fluorinated alcohols and unimolecular loss of HF from chemically activated fluoroalkoxide ions, Int. J. Mass Spectrom. Ion Phys., 1980, 33, 21. [all data]

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]


Notes

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