2-Propanone, 1,1,1,3,3,3-hexafluoro-
- Formula: C3F6O
- Molecular weight: 166.0219
- IUPAC Standard InChIKey: VBZWSGALLODQNC-UHFFFAOYSA-N
- CAS Registry Number: 684-16-2
- 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: Hexafluoroacetone; GC 7887; Perfluoro-2-propanone; Perfluoroacetone; (CF3)2CO; Hexafluoropropanone; Acetone, hexafluoro-; NCI-C56440; 1,1,1,3,3,3-Hexafluoro-2-propanone; 6FK; UN 2420; 2-Propanone, hexafluoro-; NSC 202438
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Gas phase 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.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -1433. | kJ/mol | Semi | Stewart, 2004 |
Condensed phase 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 by: Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
S°liquid | 286.60 | J/mol*K | N/A | Plaush and Pace, 1967 |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
181.29 | 245. | Plaush and Pace, 1967 | T = 12 to 244 K. |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 247.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 245.7 | K | N/A | PCR Inc., 1990 | BS |
Tboil | 245.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 147.70 | K | N/A | Plaush and Pace, 1967, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 357.14 | K | N/A | Mousa, Kay, et al., 1972 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 28.320 | bar | N/A | Mousa, Kay, et al., 1972 | Uncertainty assigned by TRC = 0.0344 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.04 | mol/l | N/A | Mousa, Kay, et al., 1972 | Uncertainty assigned by TRC = 0.0304 mol/l; TRC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
21.615 | 245.87 | Plaush and Pace, 1967 | P = 101.325 kPa; DH |
Entropy of vaporization
ΔvapS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
87.91 | 245.87 | Plaush and Pace, 1967 | P; DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
194.36 to 246.04 | 3.76719 | 723.178 | -53.618 | Plaush and Pace, 1967 | Coefficents calculated by NIST from author's data. |
239.84 to 357.3 | 4.36104 | 978.564 | -20.953 | Murphy, 1964 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.3826 | 147.70 | Plaush and Pace, 1967 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
56.75 | 147.70 | Plaush and Pace, 1967 | DH |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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- + C3F6O = (F- • C3F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 208. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1985 | 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,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Larson and McMahon, 1985 | gas phase; switching reaction,Thermochemical ladder(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 174. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1985 | 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,M |
By formula: Cl- + C3F6O = (Cl- • C3F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 120. ± 4.2 | kJ/mol | TDAs | Bofdanov and McMahon, 2002 | gas phase; B |
ΔrH° | 95.8 ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1985 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 92. | J/mol*K | N/A | Larson and McMahon, 1985 | gas phase; switching reaction,Thermochemical ladder(t-C4H9OH), Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 73.6 ± 4.2 | kJ/mol | TDAs | Bofdanov and McMahon, 2002 | gas phase; B |
ΔrG° | 68.2 ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1985 | gas phase; B,M |
ΔrG° | 68.2 | kJ/mol | ICR | Larson and McMahon, 1984 | gas phase; switching reaction(Cl-)(C2H5)3B; M |
By formula: CH3+ + C3F6O = (CH3+ • C3F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 245. | kJ/mol | PHPMS | McMahon, Heinis, et al., 1988 | gas phase; switching reaction(CH3+)N2, Entropy change calculated or estimated, uses MCA(N2) = 202. kJ/mol; Foster, Williamson, et al., 1974; M |
By formula: C9H12O + C3F6O = C12H12F6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -56.5 | kJ/mol | Eqk | N/A | liquid phase; solvent: Ethyl acetate; Flourene NMR; ALS |
(CAS Reg. No. 44870-01-1 • 4294967295) +
= CAS Reg. No. 44870-01-1
By formula: (CAS Reg. No. 44870-01-1 • 4294967295C3F6O) + C3F6O = CAS Reg. No. 44870-01-1
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 346. ± 23. | kJ/mol | N/A | Taft, Koppel, et al., 1990 | gas phase; B |
By formula: C3H2F6O2 = C3F6O + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 85.4 ± 0.8 | kJ/mol | Cm | Rogers and Rapiejko, 1971 | solid phase; Hydration; ALS |
By formula: C4H4F6O2 = CH4O + C3F6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 89. ± 1. | kJ/mol | Cm | Rogers and Rapiejko, 1971 | liquid phase; Hydration; ALS |
By formula: C3H6 + C3F6O = C6H6F6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -78.2 ± 4.2 | kJ/mol | Eqk | Moore, 1971 | gas phase; ALS |
Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 11.57 ± 0.13 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 670.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 639.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
>0.442316 | IMRB | McDonald and Chowdhury, 1985 | G3MP2B3 calculations indicate an EA of ca. 1.3 eV; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.44 | PE | Brundle, Robin, et al., 1972 | LLK |
11.68 | PE | Dewar and Worley, 1969 | RDSH |
12.09 ± 0.02 | PE | Young and Cheng, 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CF3+ | 13.8 | ? | EI | Majer, Olavesen, et al., 1971 | LLK |
CF3+ | 14.26 ± 0.10 | ? | EI | Harland and Thynne, 1970 | RDSH |
C2OF3+ | 11.65 | ? | EI | Majer, Olavesen, et al., 1971 | LLK |
C2OF3+ | 12.04 ± 0.12 | ? | EI | Harland and Thynne, 1970 | RDSH |
C3OF5+ | 16. | ? | EI | Majer, Olavesen, et al., 1971 | LLK |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
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: CH3+ + C3F6O = (CH3+ • C3F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 245. | kJ/mol | PHPMS | McMahon, Heinis, et al., 1988 | gas phase; switching reaction(CH3+)N2, Entropy change calculated or estimated, uses MCA(N2) = 202. kJ/mol; Foster, Williamson, et al., 1974; M |
By formula: Cl- + C3F6O = (Cl- • C3F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 120. ± 4.2 | kJ/mol | TDAs | Bofdanov and McMahon, 2002 | gas phase; B |
ΔrH° | 95.8 ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1985 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 92. | J/mol*K | N/A | Larson and McMahon, 1985 | gas phase; switching reaction,Thermochemical ladder(t-C4H9OH), Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 73.6 ± 4.2 | kJ/mol | TDAs | Bofdanov and McMahon, 2002 | gas phase; B |
ΔrG° | 68.2 ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1985 | gas phase; B,M |
ΔrG° | 68.2 | kJ/mol | ICR | Larson and McMahon, 1984 | gas phase; switching reaction(Cl-)(C2H5)3B; M |
By formula: F- + C3F6O = (F- • C3F6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 208. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1985 | 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,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Larson and McMahon, 1985 | gas phase; switching reaction,Thermochemical ladder(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 174. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1985 | 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,M |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Stewart, 2004
Stewart, J.J.P.,
Comparison of the accuracy of semiempirical and some DFT methods for predicting heats of formation,
J. Mol. Model, 2004, 10, 1, 6-10, https://doi.org/10.1007/s00894-003-0157-6
. [all data]
Plaush and Pace, 1967
Plaush, A.C.; Pace, E.L.,
Thermodynamic properties of hexafluoroacetone from 12K to its normal boiling point. An estimate of the barrier to internal rotation from the entropy of the gas,
J. Chem. Phys., 1967, 47, 44-48. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
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]
Plaush and Pace, 1967, 2
Plaush, A.C.; Pace, E.L.,
Thermodynamic properties of hexafluoroacetone from 12 k to its normal boiling point an estimate of the barrier to internal rotation from the entropy of the gas,
J. Chem. Phys., 1967, 47, 44-8. [all data]
Mousa, Kay, et al., 1972
Mousa, A.H.N.; Kay, W.B.; Kreglewski, A.,
The critical constants of binary mixtures of certain perfluoro-compounds with alkanes,
J. Chem. Thermodyn., 1972, 4, 301-11. [all data]
Murphy, 1964
Murphy, Kevin P.,
The Vapor Pressure of Hexoafluoro and Pentafluorochloroacetone.,
J. Chem. Eng. Data, 1964, 9, 2, 259-260, https://doi.org/10.1021/je60021a041
. [all data]
Larson and McMahon, 1985
Larson, J.W.; McMahon, T.B.,
Fluoride and chloride affinities of the main group oxides, fluorides, oxofluorides, and alkyls. Quantitative scales of lewis acidities from ICR halide exchange equilibria,
J. Am. Chem. Soc., 1985, 107, 766. [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]
Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P.,
Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions,
J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014
. [all data]
Bofdanov and McMahon, 2002
Bofdanov, B.; McMahon, T.B.,
Structures, Thermochemistry, and Infrared Spectra of Chloride Ion-Fluorinated Acetone Complexes and Neutral Fluorinated Acetones in the Gas Phase: Experiment and Theory,
Int. J. Mass Spectrom., 2002, 219, 3, 593-613, https://doi.org/10.1016/S1387-3806(02)00745-5
. [all data]
Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B.,
Fluoride and chloride affinities of main group oxides, fluorides, oxofluorides, and alkyls. Quantitative scales of lewis acidities from ion cyclotron resonance halide-exchange equilibria,
J. Phys. Chem., 1984, 88, 1083. [all data]
McMahon, Heinis, et al., 1988
McMahon, T.; Heinis, T.; Nicol, G.; Hovey, J.K.; Kebarle, P.,
Methyl Cation Affinities,
J. Am. Chem. Soc., 1988, 110, 23, 7591, https://doi.org/10.1021/ja00231a002
. [all data]
Foster, Williamson, et al., 1974
Foster, M.S.; Williamson, A.D.; Beauchamp, J.L.,
Photoionization mass spectrometry of trans-azomethane,
Int. J. Mass Spectrom. Ion Phys., 1974, 15, 429. [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]
Rogers and Rapiejko, 1971
Rogers, F.E.; Rapiejko, R.J.,
Thermochemistry of carbonyl addition reactions. I. Addition of water and methanol to hexafluoroacetone,
J. Am. Chem. Soc., 1971, 93, 4596-1597. [all data]
Moore, 1971
Moore, L.O.,
Kinetics and thermodynamic data for the hydrogen fluoride addition to vinyl fluoride,
Can. J. Chem., 1971, 49, 2471-2475. [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]
McDonald and Chowdhury, 1985
McDonald, R.N.; Chowdhury, A.K.,
Gas-Phase Ion-Molecule Reactions of Dioxygen Anion Radical (O2-.),
J. Am. Chem. Soc., 1985, 107, 14, 4123, https://doi.org/10.1021/ja00300a005
. [all data]
Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A.; Basch, H.,
Perfluoro effect in photoelectron spectroscopy. I. Nonaromatic molecules,
J. Am. Chem. Soc., 1972, 94, 1451. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Young and Cheng, 1976
Young, V.Y.; Cheng, K.L.,
The photoelectron spectra of halogen substituted acetones,
J. Chem. Phys., 1976, 65, 3187. [all data]
Majer, Olavesen, et al., 1971
Majer, J.R.; Olavesen, C.; Robb, J.C.,
Wavelength effect in the photolysis of halogenated ketones,
J. Chem. Soc. B, 1971, 48. [all data]
Harland and Thynne, 1970
Harland, P.; Thynne, J.C.J.,
Positive and negative ion formation in hexafluoroacetone by electron impact,
J. Phys. Chem., 1970, 74, 52. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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 ΔvapS Entropy of vaporization ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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