3-Hexanone

• Formula: C₆H₁₂O
• Molecular weight: 100.1589
• IUPAC Standard InChI: InChI=1S/C6H12O/c1-3-5-6(7)4-2/h3-5H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: PFCHFHIRKBAQGU-UHFFFAOYSA-N Copy
• CAS Registry Number: 589-38-8
• 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: Ethyl propyl ketone; Hexan-3-one; n-C3H7COC2H5; Hexanone-(3); Aethylpropylketon; Ethyl n-propyl ketone
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• Information on this page:
  • 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)
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

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 by: 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

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₆H₁₂O = (CH₆N⁺ • C₆H₁₂O)

Bond type: Hydrogen bonds of the type NH+-O between organics

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

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

Ionization energy determinations

Appearance energy determinations

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 by: 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

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₆H₁₂O = (CH₆N⁺ • C₆H₁₂O)

Bond type: Hydrogen bonds of the type NH+-O between organics

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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Additional Data

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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Additional Data

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.

Harrop, Head, et al., 1970
Harrop, D.; Head, A.J.; Lewis, G.B., Thermodynamic properties of organic oxygen compounds. 22. Enthalpies of combustion of some aliphatic ketones, J. Chem. Thermodyn., 1970, 2, 203-210. [all data]

Andon R.J.L., 1970
Andon R.J.L., Thermodynamic properties of organic oxygen compounds. Part XXIII. Low-temperature heat capacity and entropy of C6, C7, and C9 ketones, J. Chem. Soc. A, 1970, 833-837. [all data]

Hales J.L., 1967
Hales J.L., Thermodynamic properties of organic oxygen compounds. Part 18. Vapor heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether, Trans. Faraday Soc., 1967, 63, 1876-1879. [all data]

Andon, Counsell, et al., 1970
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XXIII. Low-temperature heat capacity and entropy of C₆, C₇, and C9 ketones, 1970, J. [all data]

Collerson, Counsell, et al., 1965
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S., 677. Thermodynamic properties of organic oxygen compounds. Part XV. Purification and vapour pressures of some ketones and ethers, J. Chem. Soc., 1965, 3697, https://doi.org/10.1039/jr9650003697 . [all data]

Andon, Counsell, et al., 1970, 2
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F., Thermodynamic Properties of Organic Oxygen Compounds Part XXIII. Low- temperature Heat Capacity and Entropy of C6, C7, and C9 Ketones, J. Chem. Soc. A, 1970, 1970, 833. [all data]

Pulliam, Gude, et al., 1994
Pulliam, M.K.; Gude, M.T.; Teja, A.S., The Critical Properties of Twelve Isomeric n-Alkanones with Six to Nine Carbon Atoms, Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties, 1994, 1994, DIPPR Data Ser. No. 2, p. 184-87. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Ambrose, Broderick, et al., 1974
Ambrose, D.; Broderick, B.E.; Townsend, R., The Critical Temperatures and Pressures of Thirty Organic Compounds, J. Appl. Chem. Biotechnol., 1974, 24, 359. [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]

Ambrose, Ellender, et al., 1975
Ambrose, D.; Ellender, J.H.; Lees, E.B.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XXXVIII. Vapour pressures of some aliphatic ketones, The Journal of Chemical Thermodynamics, 1975, 7, 5, 453-472, https://doi.org/10.1016/0021-9614(75)90275-X . [all data]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Hales, Lees, et al., 1967
Hales, J.L.; Lees, E.B.; Ruxton, D.J., Thermodynamic properties of organic oxygen compounds. Part 18.-Vapour heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether, Trans. Faraday Soc., 1967, 63, 1876. [all data]

Collerson, Counsell, et al., 1965, 2
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S., Thermodynamic Properties of Organic Oxygen Compounds. Part XV. Purification and Vapour Pressures of Some Ketones and Ethers, J. Chem. Soc., 1965, 3697-3700, https://doi.org/10.1039/jr9650003697 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [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]

Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P., Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations, Can. J. Chem., 1981, 59, 80. [all data]

Ashmore and Burgess, 1978
Ashmore, F.S.; Burgess, A.R., Photoelectron spectra of the unbranched C₅-C₇ alkenes, aldehydes and ketones, J. Chem. Soc. Faraday Trans. 2, 1978, 74, 734. [all data]

Yeo and Williams, 1969
Yeo, A.N.H.; Williams, D.H., Internal hydrogen rearrangement as a function of ion lifetime in the mass spectra of aliphatic ketones, J. Am. Chem. Soc., 1969, 91, 3582. [all data]

Holmes and Lossing, 1980
Holmes, J.L.; Lossing, F.P., Gas-phase heats of formation of keto and enol ions of carbonyl compounds., J. Am. Chem. Soc., 1980, 102, 1591. [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, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°gas	Entropy of gas at standard conditions
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  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
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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