1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)-2-propanol
- Formula: C4HF9O
- Molecular weight: 236.0358
- IUPAC Standard InChI: InChI=1S/C4HF9O/c5-2(6,7)1(14,3(8,9)10)4(11,12)13/h14H
- 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, 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 |
References
Go To: Top, Reaction thermochemistry 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]
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
Go To: Top, Reaction thermochemistry data, 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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