2-Propanol, 1,1,1,3,3,3-hexafluoro-

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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

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Individual Reactions

Fluorine anion + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (Fluorine anion • 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: F- + C3H2F6O = (F- • C3H2F6O)

Quantity Value Units Method Reference Comment
Δr47.0 ± 2.0kcal/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
Δr38.9 ± 2.0kcal/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

Chlorine anion + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (Chlorine anion • 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: Cl- + C3H2F6O = (Cl- • C3H2F6O)

Quantity Value Units Method Reference Comment
Δr26.5kcal/molICRLarson and McMahon, 1984gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, ΔrH>; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Δr25.0cal/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, ΔrH>; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Δr19.0kcal/molICRLarson and McMahon, 1984gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, ΔrH>; Larson and McMahon, 1984, 2; M

CN- + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (CN- • 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: CN- + C3H2F6O = (CN- • C3H2F6O)

Quantity Value Units Method Reference Comment
Δr25.0 ± 3.5kcal/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Δr26.cal/mol*KN/ALarson and McMahon, 1987gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M
Quantity Value Units Method Reference Comment
Δr16.8 ± 2.3kcal/molIMRELarson and McMahon, 1987gas phase; B,M

C3HF6O- + Hydrogen cation = 2-Propanol, 1,1,1,3,3,3-hexafluoro-

By formula: C3HF6O- + H+ = C3H2F6O

Quantity Value Units Method Reference Comment
Δr345.0 ± 2.1kcal/molG+TSTaft, Koppel, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Δr338.4 ± 2.0kcal/molIMRETaft, Koppel, et al., 1990gas phase; B
Δr340.40kcal/molIMRBKoppel, Pikver, et al., 1981gas phase; B

Iodide + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (Iodide • 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: I- + C3H2F6O = (I- • C3H2F6O)

Quantity Value Units Method Reference Comment
Δr23.9 ± 1.0kcal/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Quantity Value Units Method Reference Comment
Proton affinity (review)164.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity156.8kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
11.94PEKoppel, Molder, et al., 1983LBLHLM
12.23PERobin and Kuebler, 1973Vertical value; LLK

De-protonation reactions

C3HF6O- + Hydrogen cation = 2-Propanol, 1,1,1,3,3,3-hexafluoro-

By formula: C3HF6O- + H+ = C3H2F6O

Quantity Value Units Method Reference Comment
Δr345.0 ± 2.1kcal/molG+TSTaft, Koppel, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Δr338.4 ± 2.0kcal/molIMRETaft, Koppel, et al., 1990gas phase; B
Δr340.40kcal/molIMRBKoppel, Pikver, et al., 1981gas phase; B

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.

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]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [all data]

Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids, J. Am. Chem. Soc., 1987, 109, 6230. [all data]

Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P., Hydration of CN-, NO2-, NO3-, and HO- in the gas phase, Can. J. Chem., 1971, 49, 3308. [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]

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Koppel, Molder, et al., 1983
Koppel, I.A.; Molder, U.H.; Pikver, R.J., Photoelectron spectra of molecules. I. Alcohols, Org. React. Tartu, 1983, 20, 45. [all data]

Robin and Kuebler, 1973
Robin, M.B.; Kuebler, N.A., Excited electronic states of the simple alcohols, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 13. [all data]


Notes

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