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Cyclobutanone

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Gas phase thermochemistry data

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

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

Quantity Value Units Method Reference Comment
Deltafgas-91.6kJ/molCcbRocek and Radkowsky, 1973ALS
Deltafgas-101. ± 1.kJ/molCcbWolf, 1972ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
38.5350.Thermodynamics Research Center, 1997p=1 bar. Selected entropies and heat capacities are different from statistical values calculated by [ Andreevskii D.N., 1976] within 1.7-4.5 J/mol*K for S(T) and 3.8-6.4 J/mol*K for Cp(T).; GT
40.51100.
45.50150.
53.12200.
68.36273.15
74.31298.15
74.76300.
99.19400.
121.32500.
139.91600.
155.34700.
168.19800.
178.96900.
188.011000.
195.661100.
202.131200.
207.61300.
212.31400.
216.31500.

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

Quantity Value Units Method Reference Comment
Deltafliquid-131.kJ/molCcbRocek and Radkowsky, 1973 
Deltafliquid-139.5 ± 1.2kJ/molCcbWolf, 1972 
Quantity Value Units Method Reference Comment
Deltacliquid-2300.7 ± 0.63kJ/molCcbRocek and Radkowsky, 1973Corresponding «DELTA»fliquid = -130.8 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-2292.1 ± 1.2kJ/molCcbWolf, 1972Corresponding «DELTA»fliquid = -139.47 kJ/mol (simple calculation by NIST; no Washburn corrections)

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

Quantity Value Units Method Reference Comment
Tboil372.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil1171.15KN/ASieja, 1972Uncertainty assigned by TRC = 1.5 K; TRC
Tboil372.9KN/AWolf, 1972, 2Uncertainty assigned by TRC = 0.5 K; TRC
Tboil372.2KN/ARoberts and Sauer, 1949Uncertainty assigned by TRC = 4. K; TRC
Quantity Value Units Method Reference Comment
Deltavap38.3kJ/molVWiberg, Morgan, et al., 1994ALS
Deltavap38.4kJ/molAStephenson and Malanowski, 1987Based on data from 283. - 313. K.; AC
Deltavap38.2 ± 0.42kJ/molVWolf, 1972ALS
Deltavap38.2 ± 0.4kJ/molN/AWolf, 1972AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
37.7322.EBWiberg, Morgan, et al., 1994Based on data from 301. - 344. K.; AC
36.3332.A,EBStephenson and Malanowski, 1987Based on data from 317. - 380. K. See also Meyer and Hotz, 1976.; AC
38.5273.N/ABenson and Kistiakowsky, 1942Based on data from 249. - 298. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
249.09 - 298.395.003241740.994-19.419Benson and Kistiakowsky, 1942Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
10.8220.5Gonthier-Vassal and Szwarc, 1998AC

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
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- + Hydrogen cation = Cyclobutanone

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Deltar1536. ± 17.kJ/molG+TSBrickhouse and Squires, 1988gas phase; Between Me2C=NOH, EtCHO; B
Quantity Value Units Method Reference Comment
Deltar1502. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; Between Me2C=NOH, EtCHO; B

Cyclobutanone + Hydrogen = Cyclobutanol

By formula: C4H6O + H2 = C4H8O

Quantity Value Units Method Reference Comment
Deltar-67.91 ± 0.75kJ/molChydWiberg, Crocker, et al., 1991liquid phase; ALS
Deltar-53. ± 1.kJ/molChydWiberg, Crocker, et al., 1991gas phase; ALS

1,1-Dimethoxybutane + Water = Cyclobutanone + 2Methyl Alcohol

By formula: C6H12O2 + H2O = C4H6O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar25.4 ± 0.3kJ/molCmWiberg, Morgan, et al., 1994liquid phase; ALS

Cyclobutanone + 2Methyl Alcohol = 1,1-Dimethoxybutane + Water

By formula: C4H6O + 2CH4O = C6H12O2 + H2O

Quantity Value Units Method Reference Comment
Deltar-52.7 ± 1.7kJ/molCmWiberg, Morgan, et al., 1994gas 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C4H6O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.354eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)802.5kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity772.7kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.000999EFDDesfrancois, Abdoul-Carime, et al., 1994EA: 1.0 meV. Dipole-bound state.; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.4 ± 0.1EIRothgery, Holt, et al., 1975LLK
9.6 ± 0.1EIBranton and Pua, 1973LLK
9.354SWhitlock and Duncan, 1971LLK
9.61 ± 0.02PEChadwick, Frost, et al., 1971Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H2O+10.53 ± 0.15C2H4EIBranton and Pua, 1973LLK
C3H6+9.85 ± 0.15COEIBranton and Pua, 1973LLK

De-protonation reactions

C4H5O- + Hydrogen cation = Cyclobutanone

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Deltar1536. ± 17.kJ/molG+TSBrickhouse and Squires, 1988gas phase; Between Me2C=NOH, EtCHO; B
Quantity Value Units Method Reference Comment
Deltar1502. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; Between Me2C=NOH, EtCHO; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, References, Notes

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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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 118863

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.


UV/Visible spectrum

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), References, Notes

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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UVVis spectrum
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Additional Data

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Source missing citation
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 1408
Instrument Cary 14R
Melting point -50.9
Boiling point 99

References

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, Notes

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]


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, References