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2-Propanone, 1,1,1,3,3,3-hexafluoro-

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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
Deltafgas-342.6kcal/molSemiStewart, 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
liquid68.499cal/mol*KN/APlaush and Pace, 1967 

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
43.329245.Plaush and Pace, 1967T = 12 to 244 K.

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

Fluorine anion + 2-Propanone, 1,1,1,3,3,3-hexafluoro- = (Fluorine anion bullet 2-Propanone, 1,1,1,3,3,3-hexafluoro-)

By formula: F- + C3F6O = (F- bullet C3F6O)

Quantity Value Units Method Reference Comment
Deltar49.7 ± 2.0kcal/molIMRELarson and McMahon, 1985gas 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
Deltar27.cal/mol*KN/ALarson and McMahon, 1985gas phase; switching reaction,Thermochemical ladder(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Deltar41.6 ± 2.0kcal/molIMRELarson and McMahon, 1985gas 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

Chlorine anion + 2-Propanone, 1,1,1,3,3,3-hexafluoro- = (Chlorine anion bullet 2-Propanone, 1,1,1,3,3,3-hexafluoro-)

By formula: Cl- + C3F6O = (Cl- bullet C3F6O)

Quantity Value Units Method Reference Comment
Deltar28.8 ± 1.0kcal/molTDAsBofdanov and McMahon, 2002gas phase; B
Deltar22.9 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar22.cal/mol*KN/ALarson and McMahon, 1985gas phase; switching reaction,Thermochemical ladder(t-C4H9OH), Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar17.6 ± 1.0kcal/molTDAsBofdanov and McMahon, 2002gas phase; B
Deltar16.3 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase; B,M
Deltar16.3kcal/molICRLarson and McMahon, 1984gas phase; switching reaction(Cl-)(C2H5)3B; M

Methyl cation + 2-Propanone, 1,1,1,3,3,3-hexafluoro- = (Methyl cation bullet 2-Propanone, 1,1,1,3,3,3-hexafluoro-)

By formula: CH3+ + C3F6O = (CH3+ bullet C3F6O)

Quantity Value Units Method Reference Comment
Deltar58.5kcal/molPHPMSMcMahon, Heinis, et al., 1988gas phase; switching reaction(CH3+)N2, Entropy change calculated or estimated, uses MCA(N2) = 48.3 kcal/mol; Foster, Williamson, et al., 1974; M

Isopropylphenol + 2-Propanone, 1,1,1,3,3,3-hexafluoro- = 2-Propanol, 1,1,1,3,3,3-hexafluoro-2-[2-(1-methylethyl)phenoxy]-

By formula: C9H12O + C3F6O = C12H12F6O2

Quantity Value Units Method Reference Comment
Deltar-13.5kcal/molEqkN/Aliquid phase; solvent: Ethyl acetate; Flourene NMR; ALS

(CAS Reg. No. 44870-01-1 bullet 42949672952-Propanone, 1,1,1,3,3,3-hexafluoro-) + 2-Propanone, 1,1,1,3,3,3-hexafluoro- = CAS Reg. No. 44870-01-1

By formula: (CAS Reg. No. 44870-01-1 bullet 4294967295C3F6O) + C3F6O = CAS Reg. No. 44870-01-1

Quantity Value Units Method Reference Comment
Deltar82.6 ± 5.5kcal/molN/ATaft, Koppel, et al., 1990gas phase; B

1,1,1,3,3,3-hexafluoropropane-2,2-diol = 2-Propanone, 1,1,1,3,3,3-hexafluoro- + Water

By formula: C3H2F6O2 = C3F6O + H2O

Quantity Value Units Method Reference Comment
Deltar20.4 ± 0.2kcal/molCmRogers and Rapiejko, 1971solid phase; Hydration; ALS

1,1,1,3,3,3-Hexafluoro-2-methoxy-2-propanol = Methyl Alcohol + 2-Propanone, 1,1,1,3,3,3-hexafluoro-

By formula: C4H4F6O2 = CH4O + C3F6O

Quantity Value Units Method Reference Comment
Deltar21.3 ± 0.3kcal/molCmRogers and Rapiejko, 1971liquid phase; Hydration; ALS

Propene + 2-Propanone, 1,1,1,3,3,3-hexafluoro- = 4-Penten-2-ol, 1,1,1-trifluoro-2-(trifluoromethyl)-

By formula: C3H6 + C3F6O = C6H6F6O

Quantity Value Units Method Reference Comment
Deltar-18.7 ± 1.0kcal/molEqkMoore, 1971gas phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]

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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References