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
Δfgas-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.

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
Tboil247.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil245.7KN/APCR Inc., 1990BS
Tboil245.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Ttriple147.70KN/APlaush and Pace, 1967, 2Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc357.14KN/AMousa, Kay, et al., 1972Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Pc27.950atmN/AMousa, Kay, et al., 1972Uncertainty assigned by TRC = 0.0340 atm; TRC
Quantity Value Units Method Reference Comment
ρc3.04mol/lN/AMousa, Kay, et al., 1972Uncertainty assigned by TRC = 0.0304 mol/l; TRC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Reference Comment
5.1661245.87Plaush and Pace, 1967P = 101.325 kPa; DH

Entropy of vaporization

ΔvapS (cal/mol*K) Temperature (K) Reference Comment
21.01245.87Plaush and Pace, 1967P; DH

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
194.36 to 246.043.76148723.178-53.618Plaush and Pace, 1967Coefficents calculated by NIST from author's data.
239.84 to 357.34.35533978.564-20.953Murphy, 1964Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.0035147.70Plaush and Pace, 1967DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
13.56147.70Plaush and Pace, 1967DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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 • 2-Propanone, 1,1,1,3,3,3-hexafluoro-)

By formula: F- + C3F6O = (F- • C3F6O)

Quantity Value Units Method Reference Comment
Δr49.7 ± 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
Δr27.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
Δr41.6 ± 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 • 2-Propanone, 1,1,1,3,3,3-hexafluoro-)

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

Quantity Value Units Method Reference Comment
Δr28.8 ± 1.0kcal/molTDAsBofdanov and McMahon, 2002gas phase; B
Δr22.9 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase; B,M
Quantity Value Units Method Reference Comment
Δr22.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
Δr17.6 ± 1.0kcal/molTDAsBofdanov and McMahon, 2002gas phase; B
Δr16.3 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase; B,M
Δr16.3kcal/molICRLarson and McMahon, 1984gas phase; switching reaction(Cl-)(C2H5)3B; M

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

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

Quantity Value Units Method Reference Comment
Δr58.5kcal/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
Δr-13.5kcal/molEqkN/Aliquid phase; solvent: Ethyl acetate; Flourene NMR; ALS

(CAS Reg. No. 44870-01-1 • 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 • 4294967295C3F6O) + C3F6O = CAS Reg. No. 44870-01-1

Quantity Value Units Method Reference Comment
Δr82.6 ± 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
Δr20.4 ± 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
Δr21.3 ± 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
Δr-18.7 ± 1.0kcal/molEqkMoore, 1971gas 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 ± 0.13eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)160.2kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity152.9kcal/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
>0.442316IMRBMcDonald and Chowdhury, 1985G3MP2B3 calculations indicate an EA of ca. 1.3 eV; B

Ionization energy determinations

IE (eV) Method Reference Comment
11.44PEBrundle, Robin, et al., 1972LLK
11.68PEDewar and Worley, 1969RDSH
12.09 ± 0.02PEYoung and Cheng, 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CF3+13.8?EIMajer, Olavesen, et al., 1971LLK
CF3+14.26 ± 0.10?EIHarland and Thynne, 1970RDSH
C2OF3+11.65?EIMajer, Olavesen, et al., 1971LLK
C2OF3+12.04 ± 0.12?EIHarland and Thynne, 1970RDSH
C3OF5+16.?EIMajer, Olavesen, et al., 1971LLK

Ion clustering 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:
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

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

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

Quantity Value Units Method Reference Comment
Δr58.5kcal/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

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

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

Quantity Value Units Method Reference Comment
Δr28.8 ± 1.0kcal/molTDAsBofdanov and McMahon, 2002gas phase; B
Δr22.9 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase; B,M
Quantity Value Units Method Reference Comment
Δr22.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
Δr17.6 ± 1.0kcal/molTDAsBofdanov and McMahon, 2002gas phase; B
Δr16.3 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase; B,M
Δr16.3kcal/molICRLarson and McMahon, 1984gas phase; switching reaction(Cl-)(C2H5)3B; M

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

By formula: F- + C3F6O = (F- • C3F6O)

Quantity Value Units Method Reference Comment
Δr49.7 ± 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
Δr27.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
Δr41.6 ± 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

IR Spectrum

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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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

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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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, 1990.
NIST MS number 118849

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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, IR Spectrum, 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.

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

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