Cyclobutanone

• Formula: C₄H₆O
• Molecular weight: 70.0898
• IUPAC Standard InChI: InChI=1S/C4H6O/c5-4-2-1-3-4/h1-3H2 Copy

  
• IUPAC Standard InChIKey: SHQSVMDWKBRBGB-UHFFFAOYSA-N Copy
• CAS Registry Number: 1191-95-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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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
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

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

C₄H₅O^- +  =

By formula: C₄H₅O^- + H⁺ = C₄H₆O

 +  =

By formula: C₄H₆O + H₂ = C₄H₈O

 +  =  + 2

By formula: C₆H₁₂O₂ + H₂O = C₄H₆O + 2CH₄O

 + 2 =  + 

By formula: C₄H₆O + 2CH₄O = C₆H₁₂O₂ + H₂O

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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₄H₆O⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₅O^- +  =

By formula: C₄H₅O^- + H⁺ = C₄H₆O

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (2% IN CCl4 FOR 3800-1333, 2% IN CS2 FOR 1333-450 CM^-1); DOW KBr FOREPRISM-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; HP-GC/MS/IRD

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

Gas Chromatography

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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

Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, custom temperature program

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References

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

Rocek and Radkowsky, 1973
Rocek, J.; Radkowsky, A.E., Mechanism of the chromic acid oxidation of cyclobutanol, J. Am. Chem. Soc., 1973, 95, 7123-7132. [all data]

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

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Sieja, 1972
Sieja, J.B., J. Chem. Eng. Data, 1972, 17, 108. [all data]

Wolf, 1972, 2
Wolf, G., Thermochemical studies of cyclic ketones, Helv. Chim. Acta, 1972, 55, 1446. [all data]

Roberts and Sauer, 1949
Roberts, J.D.; Sauer, C.W., J. Am. Chem. Soc., 1949, 71, 3925. [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]

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]

Meyer and Hotz, 1976
Meyer, Edwin F.; Hotz, Carol A., Cohesive energies in polar organic liquids. 3. Cyclic ketones, J. Chem. Eng. Data, 1976, 21, 3, 274-279, https://doi.org/10.1021/je60070a035 . [all data]

Benson and Kistiakowsky, 1942
Benson, S.W.; Kistiakowsky, G.B., The Photochemical Decomposition of Cyclic Ketones, J. Am. Chem. Soc., 1942, 64, 1, 80-86, https://doi.org/10.1021/ja01253a021 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Gonthier-Vassal and Szwarc, 1998
Gonthier-Vassal, Anne; Szwarc, Henri, Thermodynamic properties of cycloketones: A DSC study, Thermochimica Acta, 1998, 320, 1-2, 141-154, https://doi.org/10.1016/S0040-6031(98)00409-2 . [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]

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]

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]

Rothgery, Holt, et al., 1975
Rothgery, E.F.; Holt, J.; McGee, H.A., Jr., Cryochemical synthesis and molecular energetics of cyclopropanone and some related compounds, J. Am. Chem. Soc., 1975, 97, 4971. [all data]

Branton and Pua, 1973
Branton, G.R.; Pua, C.K.N., Low energy electron impact ionization and fragmentation-cyclobutanone, Can. J. Chem., 1973, 51, 624. [all data]

Whitlock and Duncan, 1971
Whitlock, R.F.; Duncan, A.B.F., Electronic spectrum of cyclobutanone, J. Chem. Phys., 1971, 55, 218. [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]

Tello, Lebron-Aguilar, et al., 2009
Tello, A.M.; Lebron-Aguilar, R.; Quintanilla-Lopez, J.E.; Santiuste, J.M., Isothermal retention indices on poly93-cyanopropylmethyl)siloxane stationary phases, J. Chromatogr. A, 2009, 1216, 10, 1630-1639, https://doi.org/10.1016/j.chroma.2008.10.025 . [all data]

Lebrón-Aguilar, Quintanilla-López, et al., 2007
Lebrón-Aguilar, R.; Quintanilla-López, J.E.; Tello, A.M.; Santiuste, J.M., Isothermal retention indices on poly (3,3,3-trifluoropropylmethylsiloxane) stationary phases, J. Chromatogr. A, 2007, 1160, 1-2, 276-288, https://doi.org/10.1016/j.chroma.2007.05.025 . [all data]

Zenkevich, 1996
Zenkevich, I.G., Informational Maitenance of Gas Chromatographic Identification of Organic Compounds in Ecoanalytical Investigations, Z. Anal. Chem., 1996, 51, 11, 1140-1148. [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, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  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
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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