Cyclobutane

Formula: C₄H₈
Molecular weight: 56.1063
IUPAC Standard InChI: InChI=1S/C4H8/c1-2-4-3-1/h1-4H2
IUPAC Standard InChIKey: PMPVIKIVABFJJI-UHFFFAOYSA-N
CAS Registry Number: 287-23-0
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.
Isotopologues:
- Cyclobutane-d8
Other names: Tetramethylene; UN 2601
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Information on this page:
Other data available:
Data at other public NIST sites:
- Microwave spectra (on physics lab web site)
- Gas Phase Kinetics Database
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Gas phase thermochemistry data

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
8.162	50.	Dorofeeva O.V., 1986	Discrepancies between selected values and those calculated earlier [ Rathjens G.W., 1953] increase as the temperature increases and amount to 5.4 and 3.1 J/mol*K for S(1500 K) and Cp(1500 K), respectively.
9.128	100.
10.11	150.
11.67	200.
15.35	273.15
16.86 ± 0.36	298.15
16.98	300.
23.34	400.
29.166	500.
34.092	600.
38.222	700.
41.711	800.
44.692	900.
47.244	1000.
49.438	1100.
51.329	1200.
52.961	1300.
54.374	1400.
55.598	1500.

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-650.2 ± 0.1	kcal/mol	Ccb	Kaarsemaker and Coops, 1952	Corresponding Δ_fHº_liquid = 0.72 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-650.22 ± 0.1	kcal/mol	Ccb	Coops and Kaarsemaker, 1950	Corresponding Δ_fHº_liquid = 0.74 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	41.862	cal/mol*K	N/A	Rathjens and Gwinn, 1953	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
25.411	285.	Rathjens and Gwinn, 1953	T = 15 to 285 K.; DH

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
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity	Value	Units	Method	Reference	Comment
T_boil	284. ± 5.	K	AVG	N/A	Average of 9 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	183.0	K	N/A	Kaarsemaker and Coops, 1952	Uncertainty assigned by TRC = 1. K; TRC
T_fus	193.	K	N/A	Willstatter and Bruce, 1907	Uncertainty assigned by TRC = 3. K; TRC
T_fus	273.14	K	N/A	Willstatter and Bruce, 1907	Uncertainty assigned by TRC = 3. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	182.4 ± 0.6	K	AVG	N/A	Average of 12 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	5.717	kcal/mol	N/A	Majer and Svoboda, 1985
Δ_vapH°	5.54	kcal/mol	V	Kaarsemaker and Coops, 1952	ALS
Δ_vapH°	5.56 ± 0.1	kcal/mol	V	Coops and Kaarsemaker, 1950	ALS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
5.7811	285.66	N/A	Rathjens and Gwinn, 1953	P = 101.325 kPa; DH
5.782	285.7	N/A	Majer and Svoboda, 1985
6.02	272.	A	Stephenson and Malanowski, 1987	Based on data from 198. to 287. K.; AC
1.382	559.	C	Rathjens and Gwinn, 1953, 2	ALS
6.02	270.	N/A	Rathjens and Gwinn, 1953	Based on data from 217. to 285. K. See also Boublik, Fried, et al., 1984.; AC

Entropy of vaporization

Δ_vapS (cal/mol*K)	Temperature (K)	Reference	Comment
20.24	285.66	Rathjens and Gwinn, 1953	P; DH

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
213.22 to 285.34	4.06572	1038.009	-30.334	Rathjens and Gwinn, 1953	Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

Δ_subH (kcal/mol)	Temperature (K)	Method	Reference	Comment
8.70	145.	B	Bondi, 1963	AC

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
0.261	182.4	Domalski and Hearing, 1996	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
9.362	145.7	Domalski and Hearing, 1996	CAL
1.42	182.4	Domalski and Hearing, 1996	CAL

Enthalpy of phase transition

ΔH_trs (kcal/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
1.364	145.7	crystaline, II	crystaline, I	Rathjens and Gwinn, 1953	Transition over about 120 to 145.7 K. Values represent excess over extrapolated Cp curves.; DH
0.2600	182.42	crystaline, I	liquid	Rathjens and Gwinn, 1953	DH

Entropy of phase transition

ΔS_trs (cal/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
9.362	145.7	crystaline, II	crystaline, I	Rathjens and Gwinn, 1953	Transition; DH
1.42	182.42	crystaline, I	liquid	Rathjens and Gwinn, 1953	DH

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

C₄H₇^- + = Cyclobutane

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	417.4 ± 2.0	kcal/mol	Bran	DePuy, Gronert, et al., 1989	gas phase; B
Δ_rH°	419.9 ± 2.0	kcal/mol	Bran	Peerboom, Rademaker, et al., 1992	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	408.4 ± 2.1	kcal/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase; B
Δ_rG°	410.9 ± 2.1	kcal/mol	H-TS	Peerboom, Rademaker, et al., 1992	gas phase; B

2 = Cyclobutane

By formula: 2C₂H₄ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-20.7 ± 1.0	kcal/mol	Eqk	Quick, Knecht, et al., 1972	gas phase; At 750 K; ALS

Gas phase ion energetics data

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Data evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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 C₄H₈⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	9.8 ± 0.1	eV	N/A	N/A	L

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.82 ± 0.05	EI	Holmes and Lossing, 1991	LL
9.6 ± 0.1	PE	Bieri, Burger, et al., 1977	LLK
9.92 ± 0.05	PE	Raymonda, 1972	LLK
10.06	EI	Lossing, 1972	LLK
≤10.3	PI	Doepker and Ausloos, 1966	Personal communication from P. Natalis, B. Steiner, and M.G. Inghram; RDSH
10.7 ± 0.1	PE	Bieri, Burger, et al., 1977	Vertical value; LLK
10.7 ± 0.1	PE	Bischof, Haselbach, et al., 1970	Vertical value; RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₂H₂⁺	16.8	?	EI	Hughes and Tiernan, 1969	RDSH
C₂H₃⁺	17.7	?	EI	Hughes and Tiernan, 1969	RDSH
C₂H₄⁺	11.0 ± 0.15	?	EI	Meisels, Park, et al., 1970	RDSH
C₂H₅⁺	13.8	?	EI	Hughes and Tiernan, 1969	RDSH
C₃H₃⁺	14.8	?	EI	Hughes and Tiernan, 1969	RDSH
C₃H₅⁺	11.00	CH₃	EI	Lossing, 1972	LLK
C₄H₆⁺	11.2 ± 0.1	H₂	EI	Holmes, Weese, et al., 1977	LLK
C₄H₇⁺	10.91	H	EI	Lossing, 1972	LLK

De-protonation reactions

C₄H₇^- + = Cyclobutane

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	417.4 ± 2.0	kcal/mol	Bran	DePuy, Gronert, et al., 1989	gas phase; B
Δ_rH°	419.9 ± 2.0	kcal/mol	Bran	Peerboom, Rademaker, et al., 1992	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	408.4 ± 2.1	kcal/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase; B
Δ_rG°	410.9 ± 2.1	kcal/mol	H-TS	Peerboom, Rademaker, et al., 1992	gas phase; 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

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Rathjens G.W., 1953
Rathjens G.W., Jr., Infrared absorption spectra, structure and thermodynamic properties of cyclobutane, J. Am. Chem. Soc., 1953, 75, 5634-5642. [all data]

Kaarsemaker and Coops, 1952
Kaarsemaker, S.; Coops, J., Thermal quantities of some cycloparaffins. Part III. Results of measurements, Rec. Trav. Chim. Pays/Bas, 1952, 71, 261. [all data]

Coops and Kaarsemaker, 1950
Coops, J.; Kaarsemaker, SJ., Heat of combustion of cyclobutane, Recl. Trav. Chim. Pays-Bas, 1950, 69, 1364. [all data]

Rathjens and Gwinn, 1953
Rathjens, G.W., Jr.; Gwinn, W.D., Heat capacities and entropy of cyclobutane, J. Am. Chem. Soc., 1953, 75, 5629-5633. [all data]

Willstatter and Bruce, 1907
Willstatter, R.; Bruce, J., Chem. Ber., 1907, 40, 3979. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]

Rathjens and Gwinn, 1953, 2
Rathjens, G.W., Jr.; Gwinn, W.D., Heat capacities and entropy of cyclobutane, J. Am. Chem. Soc., 1953, 75, 5629-56. [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]

Bondi, 1963
Bondi, A., Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments., J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]

Quick, Knecht, et al., 1972
Quick, L.M.; Knecht, D.A.; Back, M.H., Kinetics of the formation of cyclobutane from ethylene, Int. J. Chem. Kinet., 1972, 4, 61-68. [all data]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Raymonda, 1972
Raymonda, J.W., Rydberg states in cyclic alkanes, J. Chem. Phys., 1972, 56, 3912. [all data]

Lossing, 1972
Lossing, F.P., Free radicals by mass spectrometry. XLV. Ionization potentials and heats of formation of C₃H₃, C₃H₅, and C₄H₇ radicals and ions, Can. J. Chem., 1972, 50, 3973. [all data]

Doepker and Ausloos, 1966
Doepker, R.D.; Ausloos, P., Gas-phase radiolysis of cyclobutane, J. Chem. Phys., 1966, 44, 1641. [all data]

Bischof, Haselbach, et al., 1970
Bischof, P.; Haselbach, E.; Heilbronner, E., Photoelectron spectrum of cyclobutane, Angew. Chem. Int. Ed. Engl., 1970, 9, 953. [all data]

Hughes and Tiernan, 1969
Hughes, B.M.; Tiernan, T.O., Ionic reactions in gaseous cyclobutane, J. Chem. Phys., 1969, 51, 4373. [all data]

Meisels, Park, et al., 1970
Meisels, G.G.; Park, J.Y.; Giessner, B.G., Ionization and dissociation of C₄H₈ isomers, J. Am. Chem. Soc., 1970, 92, 254. [all data]

Holmes, Weese, et al., 1977
Holmes, J.L.; Weese, G.M.; Blair, A.S.; Terlouw, J.K., Metastable ion studies IX-Thermochemistry and ion structures among fragmenting [C₄H₈]⁺ ions, an electron impact and field ionization investigation, Org. Mass Spectrom., 1977, 12, 424. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
S°_liquid	Entropy of liquid at standard conditions
T_boil	Boiling point
T_fus	Fusion (melting) point
T_triple	Triple point temperature
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_subH	Enthalpy of sublimation
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions
Δ_vapS	Entropy of vaporization

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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