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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Gas phase thermochemistry data
Go To: Top, Reaction 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 by: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
34.15 | 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. |
38.19 | 100. | ||
42.28 | 150. | ||
48.84 | 200. | ||
64.23 | 273.15 | ||
70.6 ± 1.5 | 298.15 | ||
71.05 | 300. | ||
97.67 | 400. | ||
122.03 | 500. | ||
142.64 | 600. | ||
159.92 | 700. | ||
174.52 | 800. | ||
186.99 | 900. | ||
197.67 | 1000. | ||
206.85 | 1100. | ||
214.76 | 1200. | ||
221.59 | 1300. | ||
227.50 | 1400. | ||
232.62 | 1500. |
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° | 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 |
By formula: 2C2H4 = C4H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -86.6 ± 4.2 | kJ/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° | 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)
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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, Gas phase thermochemistry data, Reaction thermochemistry 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.
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]
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, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy 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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