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


Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References, Notes

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

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
Deltar56.3 ± 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
Deltar47.9 ± 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

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
Deltar331.6 ± 2.2kcal/molG+TSTaft, Koppel, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar324.0 ± 2.0kcal/molIMRETaft, Koppel, et al., 1990gas phase; B
Deltar323.2 ± 5.0kcal/molIMRBKoppel, Pikver, et al., 1981gas phase; B
Deltar321.4 ± 5.0kcal/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
Deltar23.2 ± 1.0kcal/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Ion clustering data, Mass spectrum (electron ionization), 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

Quantity Value Units Method Reference Comment
Proton affinity (review)161.8kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity154.6kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
12.25PEKoppel, Molder, et al., 1983LBLHLM

De-protonation reactions

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
Deltar331.6 ± 2.2kcal/molG+TSTaft, Koppel, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar324.0 ± 2.0kcal/molIMRETaft, Koppel, et al., 1990gas phase; B
Deltar323.2 ± 5.0kcal/molIMRBKoppel, Pikver, et al., 1981gas phase; B
Deltar321.4 ± 5.0kcal/molIMRBClair and McMahon, 1980gas phase; B

Ion clustering data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering 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
Deltar56.3 ± 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
Deltar47.9 ± 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

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
Deltar23.2 ± 1.0kcal/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

Mass spectrum (electron ionization)

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

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin MUS23 A. Mujsce, AT&T Bell Labs., Murray Hill, N.J., USA
NIST MS number 115419

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References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), 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]

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]

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]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References