Cyclobutanone

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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

Quantity Value Units Method Reference Comment
Δfgas-21.9kcal/molCcbRocek and Radkowsky, 1973ALS
Δfgas-24.2 ± 0.3kcal/molCcbWolf, 1972ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
9.20950.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
9.682100.
10.87150.
12.70200.
16.34273.15
17.76298.15
17.87300.
23.71400.
28.996500.
33.439600.
37.127700.
40.198800.
42.772900.
44.9351000.
46.7641100.
48.3101200.
49.621300.
50.741400.
51.701500.

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
Δfliquid-31.3kcal/molCcbRocek and Radkowsky, 1973 
Δfliquid-33.34 ± 0.28kcal/molCcbWolf, 1972 
Quantity Value Units Method Reference Comment
Δcliquid-549.89 ± 0.15kcal/molCcbRocek and Radkowsky, 1973Corresponding Δfliquid = -31.26 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcliquid-547.82 ± 0.28kcal/molCcbWolf, 1972Corresponding Δfliquid = -33.334 kcal/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
Δvap9.15kcal/molVWiberg, Morgan, et al., 1994ALS
Δvap9.18kcal/molAStephenson and Malanowski, 1987Based on data from 283. to 313. K.; AC
Δvap9.14 ± 0.10kcal/molVWolf, 1972ALS
Δvap9.13 ± 0.1kcal/molN/AWolf, 1972AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
9.01322.EBWiberg, Morgan, et al., 1994Based on data from 301. to 344. K.; AC
8.68332.A,EBStephenson and Malanowski, 1987Based on data from 317. to 380. K. See also Meyer and Hotz, 1976.; AC
9.20273.N/ABenson and Kistiakowsky, 1942Based on data from 249. to 298. K. See also Boublik, Fried, et al., 1984.; AC

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
249.09 to 298.394.997531740.994-19.419Benson and Kistiakowsky, 1942Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.58220.5Gonthier-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:


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)191.8kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity184.7kcal/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
Δr367.1 ± 4.1kcal/molG+TSBrickhouse and Squires, 1988gas phase; Between Me2C=NOH, EtCHO; B
Quantity Value Units Method Reference Comment
Δr359.0 ± 4.0kcal/molIMRBBrickhouse and Squires, 1988gas phase; Between Me2C=NOH, EtCHO; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]

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]

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]


Notes

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