2-Propanol, 1,1,1,3,3,3-hexafluoro-
- Formula: C3H2F6O
- Molecular weight: 168.0378
- IUPAC Standard InChIKey: BYEAHWXPCBROCE-UHFFFAOYSA-N
- CAS Registry Number: 920-66-1
- 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: Bis(trifluoromethyl)methanol; Hexafluoroisopropanol; Hexafluoroisopropyl alcohol; 1,1,1,3,3,3-Hexafluoro-2-propanol; 1,1,1,3,3,3-Hexafluoroisopropanol; 1,1,1,3,3,3-Hexafluoroisopropyl alcohol; 2,2,2-Trifluoro-1-(trifluoromethyl)ethanol; 2H-Hexafluoroisopropanol; CF3CH(OH)CF3; 1,1,1,3,3,3-Hexafluoropropan-2-ol; Ethanol, 2,2,2-trifluoro-1-(trifluoromethyl)-; Hexafluoro-2-propanol; HFIP; 1,1,1,3,3,3-Hexafluoropropanol; 1,1,1,3,3,3-Hexafluoro-2-hydroxypropane; NSC 96336
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Phase change data
Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, 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:
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 331. | K | N/A | PCR Inc., 1990 | BS |
Tboil | 332.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 41.58 | kJ/mol | V | Rochester and Symonds, 1973 | ALS |
ΔvapH° | 41.6 | kJ/mol | MM | Rochester and Symonds, 1973 | Based on data from 294. to 330. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
40.2 | 309. | A,MM | Stephenson and Malanowski, 1987 | Based on data from 294. to 330. K. See also Rochester and Symonds, 1973.; AC |
47.3 | 284. | N/A | Van Ness, Soczek, et al., 1967 | Based on data from 273. to 296. K.; AC |
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
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- + C3H2F6O = (F- • C3H2F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 197. ± 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° | 163. ± 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: Cl- + C3H2F6O = (Cl- • C3H2F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 111. | kJ/mol | ICR | Larson and McMahon, 1984 | gas 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 |
ΔrS° | 105. | J/mol*K | N/A | Larson and McMahon, 1984 | gas 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 |
ΔrG° | 79.5 | kJ/mol | ICR | Larson and McMahon, 1984 | gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, ΔrH>; Larson and McMahon, 1984, 2; M |
By formula: CN- + C3H2F6O = (CN- • C3H2F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 105. ± 15. | kJ/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Larson and McMahon, 1987 | gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 70.3 ± 9.6 | kJ/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
C3HF6O- + =
By formula: C3HF6O- + H+ = C3H2F6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1443. ± 8.8 | kJ/mol | G+TS | Taft, Koppel, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1416. ± 8.4 | kJ/mol | IMRE | Taft, Koppel, et al., 1990 | gas phase; B |
ΔrG° | 1424.2 | kJ/mol | IMRB | Koppel, Pikver, et al., 1981 | gas phase; B |
By formula: I- + C3H2F6O = (I- • C3H2F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 100. ± 4.2 | kJ/mol | TDAs | Caldwell, Masucci, et al., 1989 | gas phase; B,M |
Henry's Law 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 by: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
24. | 6700. | M | N/A |
Gas phase ion energetics data
Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, 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) | 686.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 656.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.94 | PE | Koppel, Molder, et al., 1983 | LBLHLM |
12.23 | PE | Robin and Kuebler, 1973 | Vertical value; LLK |
De-protonation reactions
C3HF6O- + =
By formula: C3HF6O- + H+ = C3H2F6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1443. ± 8.8 | kJ/mol | G+TS | Taft, Koppel, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1416. ± 8.4 | kJ/mol | IMRE | Taft, Koppel, et al., 1990 | gas phase; B |
ΔrG° | 1424.2 | kJ/mol | IMRB | Koppel, Pikver, et al., 1981 | gas phase; B |
Ion clustering data
Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, 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: CN- + C3H2F6O = (CN- • C3H2F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 105. ± 15. | kJ/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Larson and McMahon, 1987 | gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 70.3 ± 9.6 | kJ/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
By formula: Cl- + C3H2F6O = (Cl- • C3H2F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 111. | kJ/mol | ICR | Larson and McMahon, 1984 | gas 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 |
ΔrS° | 105. | J/mol*K | N/A | Larson and McMahon, 1984 | gas 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 |
ΔrG° | 79.5 | kJ/mol | ICR | Larson and McMahon, 1984 | gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, ΔrH>; Larson and McMahon, 1984, 2; M |
By formula: F- + C3H2F6O = (F- • C3H2F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 197. ± 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° | 163. ± 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- + C3H2F6O = (I- • C3H2F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 100. ± 4.2 | kJ/mol | TDAs | Caldwell, Masucci, et al., 1989 | gas phase; B,M |
IR Spectrum
Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), NIST Free Links, 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
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
Mass spectrum (electron ionization)
Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, NIST Free Links, 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 | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 290914 |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
PCR Inc., 1990
PCR Inc.,
Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Rochester and Symonds, 1973
Rochester, C.H.; Symonds, J.R.,
Thermodynamic studies of fluoroalchols Part 1.-Vapour pressures and enthalpies of vaporization,
J. Chem. Soc. Faraday Trans. 1, 1973, 69, 1267. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Van Ness, Soczek, et al., 1967
Van Ness, Hendrick C.; Soczek, C.A.; Peloquin, G.L.; Machado, R.L.,
Thermodynamic excess properties of three alcohol-hydrocarbon systems,
J. Chem. Eng. Data, 1967, 12, 2, 217-224, https://doi.org/10.1021/je60033a017
. [all data]
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
Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, References
- Symbols used in this document:
Tboil Boiling point d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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