Cyclohexanone

• Formula: C₆H₁₀O
• Molecular weight: 98.1430
• IUPAC Standard InChI: InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2 Copy

  
• IUPAC Standard InChIKey: JHIVVAPYMSGYDF-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-94-1
• 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: Anon; Anone; Hexanon; Hytrol O; Nadone; Pimelic ketone; Pimelin ketone; Sextone; Ketohexamethylene; Cicloesanone; Cyclohexanon; Cykloheksanon; NCI-C55005; Rcra waste number U057; UN 1915; Cyclohexyl ketone; NSC 5711
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • 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

Constant pressure heat capacity of gas

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
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

C₆H₉O^- +  =

By formula: C₆H₉O^- + H⁺ = C₆H₁₀O

 +  =

By formula: C₆H₁₀O + H₂ = C₆H₁₂O

=  + 

By formula: C₆H₁₂O = C₆H₁₀O + H₂

 +  =  + 

By formula: H₂O + C₇H₁₂O = C₆H₁₀O + CH₄O

 +  =  + 2

By formula: H₂O + C₈H₁₆O₂ = C₆H₁₀O + 2CH₄O

 +  =  + 

By formula: C₆H₁₂O + C₃H₆O = C₆H₁₀O + C₃H₈O

 + 2 =  + 

By formula: C₆H₁₀O + 2CH₄O = H₂O + C₈H₁₆O₂

 +  =  + 

By formula: C₆H₁₀O + C₅H₁₀O = C₆H₁₂O + C₅H₈O

 +  =  + 

By formula: C₆H₁₀O + C₃H₈O = C₆H₁₂O + C₃H₆O

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:
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₆H₁₀O⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

De-protonation reactions

C₆H₉O^- +  =

By formula: C₆H₉O^- + H⁺ = C₆H₁₀O

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, AND 10% CCl4 FOR 650-240 CM^-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

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

UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Kabo, Yursha, et al., 1988
Kabo, G.J.; Yursha, I.A.; Frenkel, M.L.; Poleshchuk, P.A.; Fedoseenko, V.I.; Ladutko, A.I., Thermodynamic properties of cyclohexanol and cyclohexanone, J. Chem. Thermodyn., 1988, 20, 429-437. [all data]

Wolf, 1972
Wolf, G., Thermochemische Untersuchungen an cyclischen Ketonen, Helv. Chim. Acta, 1972, 55, 1446-1459. [all data]

Sellers and Sunner, 1962
Sellers, P.; Sunner, S., Heats of combustion of cyclic ketones and alcohols, Acta Chem. Scand., 1962, 16, 46-52. [all data]

Kabo G.J., 1988
Kabo G.J., Thermodynamic properties of cyclohexanol and cyclohexanone, J. Chem. Thermodyn., 1988, 20, 429-437. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Andreevskii D.N., 1976
Andreevskii D.N., Thermodynamic properties of C4-C6 cyclic ketones, Zh. Prikl. Khim., 1976, 49, 1819-1823. [all data]

Shvaro O.V., 1987
Shvaro O.V., Thermodynamic properties of cyclopentanone and cyclohexanone, Inzh.-Fiz. Zh., 1987, 52, 807-812. [all data]

Vilcu R., 1975
Vilcu R., Heat capacity of cyclohexanone and 4-methylcyclohexanone in the vapor phase, Rev. Chim. (Bucharest), 1975, 26, 129-131. [all data]

Kabo G.J., 1995
Kabo G.J., Thermodynamic properties, conformation, and phase transitions of cyclopentanol, J. Chem. Thermodyn., 1995, 27, 953-967. [all data]

Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I., Molecular Rotation and the Observation of Dipole-Bound States of Anions, J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688 . [all data]

Zimmerman, Jackson, et al., 1978
Zimmerman, A.H.; Jackson, R.L.; Janousek, B.K.; Brauman, J.J., Electron photodetachment from cyclic enolate anions in the gas phase: Electron affinities of cyclic enolate radicals, J. Am. Chem. Soc., 1978, 100, 4674. [all data]

Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R., Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions, J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002 . [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Hine and Arata, 1976
Hine, J.; Arata, K., Keto-Enol tautomerism. II. The calorimetrical determination of the equilibrium constants for keto-enol tautomerism for cyclohexanone, Bull. Chem. Soc. Jpn., 1976, 49, 3089-3092. [all data]

Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]

Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions, Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]

Fedoseenko, Yursha, et al., 1984
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium of cyclopentanol dehydrogenation and hydrogen disproportionation in the cyclopentanol-cyclohexanone system, Dokl. Akad. Nauk BSSR, 1984, 28, 1109-1112. [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]

Desfrancois, Abdoul-Carime, et al., 1994
Desfrancois, C.; Abdoul-Carime, H.; Khelifa, N.; Schermann, J.P., Fork 1/r to 1/r2 Potentials: Electron Exchange between Rydberg Atoms and Polar Molecules, Phys. Rev. Lett., 1994, 73, 18, 2436, https://doi.org/10.1103/PhysRevLett.73.2436 . [all data]

Loudet, Grimaud, et al., 1976
Loudet, M.; Grimaud, M.; Metras, F.; Pfister-Guillouzo, G., Interactions intramoleculaires en serie cyclohexanique partie II. Spectres photoelectroniques de chloro-2-cyclohexanones, J. Mol. Struct., 1976, 35, 213. [all data]

Fortin, Forest, et al., 1973
Fortin, C.J.; Forest, M.; Vaziri, C.; Gravel, D.; Rousseau, Y., Spectrometrie de masse des cyclohexanones gem-diphenylees. I. Localisation de la charge positive, Can. J. Chem., 1973, 51, 3445. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Vilesov, 1960
Vilesov, F.I., The photoionization of vapors of compounds whose molecules contain carbonyl groups, Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]

Spanka and Rademacher, 1986
Spanka, G.; Rademacher, P., Transannular interactions in difunctional medium rings. 1. n/π Interactions in cyclic amino ketones and aminoalkenes studied by photoelectron spectroscopy, J. Org. Chem., 1986, 51, 592. [all data]

Kovac and Klasinc, 1978
Kovac, B.; Klasinc, L., Photoelectron spectroscopy of adamantane and some adamantanones, Croat. Chem. Acta, 1978, 51, 55. [all data]

Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M., Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen, J. Mol. Struct., 1974, 21, 231. [all data]

Chadwick, Frost, et al., 1971
Chadwick, D.; Frost, D.C.; Weiler, L., The photoelectron spectra of cyclic ketones, Tetrahedron Lett., 1971, 47, 4543. [all data]

Grammaticakis, 1953
Grammaticakis, P., Contribution a l'etude de l'absorption dans l'U.-V. moyen et le visible des composes carbonyles aromatiques et de leurs derives. (2^e memoire), Bull. Soc. Chim. Fr., 1953, 20, 865-872. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  S°gas	Entropy of gas at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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