Cyclobutanone

Formula: C₄H₆O
Molecular weight: 70.0898
IUPAC Standard InChI: InChI=1S/C4H6O/c5-4-2-1-3-4/h1-3H2
IUPAC Standard InChIKey: SHQSVMDWKBRBGB-UHFFFAOYSA-N
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
The 3d structure may be viewed using Java or Javascript.
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Gas phase thermochemistry data

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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
Δ_fH°_gas	-21.9	kcal/mol	Ccb	Rocek and Radkowsky, 1973	ALS
Δ_fH°_gas	-24.2 ± 0.3	kcal/mol	Ccb	Wolf, 1972	ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
9.209	50.	Thermodynamics Research Center, 1997	p=1 bar. Selected entropies and heat capacities are different from statistical values calculated by [ Andreevskii D.N., 1976] within 1.7-4.5 J/molK for S(T) and 3.8-6.4 J/molK for Cp(T).; GT
9.682	100.
10.87	150.
12.70	200.
16.34	273.15
17.76	298.15
17.87	300.
23.71	400.
28.996	500.
33.439	600.
37.127	700.
40.198	800.
42.772	900.
44.935	1000.
46.764	1100.
48.310	1200.
49.62	1300.
50.74	1400.
51.70	1500.

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-31.3	kcal/mol	Ccb	Rocek and Radkowsky, 1973
Δ_fH°_liquid	-33.34 ± 0.28	kcal/mol	Ccb	Wolf, 1972
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-549.89 ± 0.15	kcal/mol	Ccb	Rocek and Radkowsky, 1973	Corresponding Δ_fHº_liquid = -31.26 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_liquid	-547.82 ± 0.28	kcal/mol	Ccb	Wolf, 1972	Corresponding Δ_fHº_liquid = -33.334 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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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
T_boil	372.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS
T_boil	1171.15	K	N/A	Sieja, 1972	Uncertainty assigned by TRC = 1.5 K; TRC
T_boil	372.9	K	N/A	Wolf, 1972, 2	Uncertainty assigned by TRC = 0.5 K; TRC
T_boil	372.2	K	N/A	Roberts and Sauer, 1949	Uncertainty assigned by TRC = 4. K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	9.15	kcal/mol	V	Wiberg, Morgan, et al., 1994	ALS
Δ_vapH°	9.18	kcal/mol	A	Stephenson and Malanowski, 1987	Based on data from 283. to 313. K.; AC
Δ_vapH°	9.14 ± 0.10	kcal/mol	V	Wolf, 1972	ALS
Δ_vapH°	9.13 ± 0.1	kcal/mol	N/A	Wolf, 1972	AC

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
9.01	322.	EB	Wiberg, Morgan, et al., 1994	Based on data from 301. to 344. K.; AC
8.68	332.	A,EB	Stephenson and Malanowski, 1987	Based on data from 317. to 380. K. See also Meyer and Hotz, 1976.; AC
9.20	273.	N/A	Benson and Kistiakowsky, 1942	Based 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 298.39	4.99753	1740.994	-19.419	Benson and Kistiakowsky, 1942	Coefficents calculated by NIST from author's data.

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
2.58	220.5	Gonthier-Vassal and Szwarc, 1998	AC

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 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^- + = Cyclobutanone

By formula: C₄H₅O^- + H⁺ = C₄H₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	367.1 ± 4.1	kcal/mol	G+TS	Brickhouse and Squires, 1988	gas phase; Between Me2C=NOH, EtCHO; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	359.0 ± 4.0	kcal/mol	IMRB	Brickhouse and Squires, 1988	gas phase; Between Me2C=NOH, EtCHO; B

Cyclobutanone + =

By formula: C₄H₆O + H₂ = C₄H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-16.23 ± 0.18	kcal/mol	Chyd	Wiberg, Crocker, et al., 1991	liquid phase; ALS
Δ_rH°	-12.7 ± 0.3	kcal/mol	Chyd	Wiberg, Crocker, et al., 1991	gas phase; ALS

+ = Cyclobutanone + 2

By formula: C₆H₁₂O₂ + H₂O = C₄H₆O + 2CH₄O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	6.07 ± 0.07	kcal/mol	Cm	Wiberg, Morgan, et al., 1994	liquid phase; ALS

Cyclobutanone + 2 = +

By formula: C₄H₆O + 2CH₄O = C₆H₁₂O₂ + H₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-12.6 ± 0.41	kcal/mol	Cm	Wiberg, Morgan, et al., 1994	gas phase; ALS

Gas phase ion energetics data

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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)	9.354	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	191.8	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	184.7	kcal/mol	N/A	Hunter and Lias, 1998	HL

Electron affinity determinations

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

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.4 ± 0.1	EI	Rothgery, Holt, et al., 1975	LLK
9.6 ± 0.1	EI	Branton and Pua, 1973	LLK
9.354	S	Whitlock and Duncan, 1971	LLK
9.61 ± 0.02	PE	Chadwick, Frost, et al., 1971	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₂H₂O⁺	10.53 ± 0.15	C₂H₄	EI	Branton and Pua, 1973	LLK
C₃H₆⁺	9.85 ± 0.15	CO	EI	Branton and Pua, 1973	LLK

De-protonation reactions

C₄H₅O^- + = Cyclobutanone

By formula: C₄H₅O^- + H⁺ = C₄H₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	367.1 ± 4.1	kcal/mol	G+TS	Brickhouse and Squires, 1988	gas phase; Between Me2C=NOH, EtCHO; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	359.0 ± 4.0	kcal/mol	IMRB	Brickhouse and Squires, 1988	gas phase; Between Me2C=NOH, EtCHO; B

References

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

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

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
EA	Electron affinity
IE (evaluated)	Recommended ionization energy
T_boil	Boiling point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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