Cyclobutane
- Formula: C4H8
- Molecular weight: 56.1063
- 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
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
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 | -2720.4 ± 0.5 | kJ/mol | Ccb | Kaarsemaker and Coops, 1952 | Corresponding ΔfHºliquid = 3.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -2720.5 ± 0.4 | kJ/mol | Ccb | Coops and Kaarsemaker, 1950 | Corresponding ΔfHºliquid = 3.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 175.15 | J/mol*K | N/A | Rathjens and Gwinn, 1953 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
106.32 | 285. | Rathjens and Gwinn, 1953 | T = 15 to 285 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
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
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 |
---|---|---|---|---|---|
Tboil | 284. ± 5. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 183.0 | K | N/A | Kaarsemaker and Coops, 1952 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 193. | K | N/A | Willstatter and Bruce, 1907 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 273.14 | K | N/A | Willstatter and Bruce, 1907 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 182.4 ± 0.6 | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 23.92 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 23.2 | kJ/mol | V | Kaarsemaker and Coops, 1952 | ALS |
ΔvapH° | 23.3 ± 0.4 | kJ/mol | V | Coops and Kaarsemaker, 1950 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
24.188 | 285.66 | N/A | Rathjens and Gwinn, 1953 | P = 101.325 kPa; DH |
24.19 | 285.7 | N/A | Majer and Svoboda, 1985 | |
25.2 | 272. | A | Stephenson and Malanowski, 1987 | Based on data from 198. to 287. K.; AC |
5.781 | 559. | C | Rathjens and Gwinn, 1953, 2 | ALS |
25.2 | 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
ΔvapS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
84.67 | 285.66 | Rathjens and Gwinn, 1953 | P; DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
213.22 to 285.34 | 4.07143 | 1038.009 | -30.334 | Rathjens and Gwinn, 1953 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
36.4 | 145. | B | Bondi, 1963 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.09 | 182.4 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.17 | 145.7 | Domalski and Hearing, 1996 | CAL |
5.96 | 182.4 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
5.707 | 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 |
1.088 | 182.42 | crystaline, I | liquid | Rathjens and Gwinn, 1953 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
39.17 | 145.7 | crystaline, II | crystaline, I | Rathjens and Gwinn, 1953 | Transition; DH |
5.96 | 182.42 | crystaline, I | liquid | Rathjens and Gwinn, 1953 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References, Notes
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° | 1746. ± 8.4 | kJ/mol | Bran | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrH° | 1757. ± 8.4 | kJ/mol | Bran | Peerboom, Rademaker, et al., 1992 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1709. ± 8.8 | kJ/mol | H-TS | DePuy, Gronert, et al., 1989 | gas phase; B |
ΔrG° | 1719. ± 8.8 | kJ/mol | H-TS | Peerboom, Rademaker, et al., 1992 | gas phase; B |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
NIST MS number | 107 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]
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]
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
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ΔvapS Entropy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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