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:
- Other names: Tetramethylene; UN 2601
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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 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 |
|---|---|---|---|---|---|
| ΔcH°liquid | -650.2 ± 0.1 | kcal/mol | Ccb | Kaarsemaker and Coops, 1952 | Corresponding ΔfHºliquid = 0.72 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -650.22 ± 0.1 | kcal/mol | Ccb | Coops and Kaarsemaker, 1950 | Corresponding ΔfHºliquid = 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
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 25.411 | 285. | Rathjens and Gwinn, 1953 | T = 15 to 285 K.; DH |
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
C4H7- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 417.4 ± 2.0 | kcal/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
| ΔrH° | 419.9 ± 2.0 | kcal/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 408.4 ± 2.1 | kcal/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
| ΔrG° | 410.9 ± 2.1 | kcal/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
2 =
By formula: 2C2H4 = C4H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -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 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:
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- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 417.4 ± 2.0 | kcal/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
| ΔrH° | 419.9 ± 2.0 | kcal/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 408.4 ± 2.1 | kcal/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
| ΔrG° | 410.9 ± 2.1 | kcal/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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.
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]
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
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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