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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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

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

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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]

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]

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]

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
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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