1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)-2-propanol
- Formula: C4HF9O
- Molecular weight: 236.0358
- IUPAC Standard InChIKey: XZNOAVNRSFURIR-UHFFFAOYSA-N
- CAS Registry Number: 2378-02-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Perfluoro-tert-butanol; (CF3)3COH; Perfluoro-t-butanol; 2-Propanol, 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-; Nonafluor-terc.butanol; Nonafluoro-tert-butanol; Ethanol, 2,2,2-trifluoro-1,1-bis(trifluoromethyl)-; perfluoro-tert-butyl alcohol
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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
By formula: F- + C4HF9O = (F- • C4HF9O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 236. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas 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 |
ΔrG° | 200. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas 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- + =
By formula: C4F9O- + H+ = C4HF9O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1387. ± 9.2 | kJ/mol | G+TS | Taft, Koppel, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1356. ± 8.4 | kJ/mol | IMRE | Taft, Koppel, et al., 1990 | gas phase; B |
ΔrG° | 1352. ± 21. | kJ/mol | IMRB | Koppel, Pikver, et al., 1981 | gas phase; B |
ΔrG° | 1345. ± 21. | kJ/mol | IMRB | Clair and McMahon, 1980 | gas phase; B |
By formula: I- + C4HF9O = (I- • C4HF9O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 97.1 ± 4.2 | kJ/mol | TDAs | Caldwell, Masucci, et al., 1989 | gas 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) | 676.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 646.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
12.25 | PE | Koppel, Molder, et al., 1983 | LBLHLM |
De-protonation reactions
C4F9O- + =
By formula: C4F9O- + H+ = C4HF9O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1387. ± 9.2 | kJ/mol | G+TS | Taft, Koppel, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1356. ± 8.4 | kJ/mol | IMRE | Taft, Koppel, et al., 1990 | gas phase; B |
ΔrG° | 1352. ± 21. | kJ/mol | IMRB | Koppel, Pikver, et al., 1981 | gas phase; B |
ΔrG° | 1345. ± 21. | kJ/mol | IMRB | Clair and McMahon, 1980 | gas 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
By formula: F- + C4HF9O = (F- • C4HF9O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 236. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas 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 |
ΔrG° | 200. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1983 | gas 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 |
By formula: I- + C4HF9O = (I- • C4HF9O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 97.1 ± 4.2 | kJ/mol | TDAs | Caldwell, Masucci, et al., 1989 | gas 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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
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
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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