Cyclobutane, methylene-
- Formula: C5H8
- Molecular weight: 68.1170
- IUPAC Standard InChIKey: QIRVGKYPAOQVNP-UHFFFAOYSA-N
- CAS Registry Number: 1120-56-5
- 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. - Species with the same structure:
- Other names: Methylenecyclobutane
- Information on this page:
- Other data available:
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Gas 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 106. | kJ/mol | Chyd | Roth, Adamczak, et al., 1991 | ALS |
ΔfH°gas | 121.5 ± 0.71 | kJ/mol | Ccb | Good, Moore, et al., 1974 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 298.9 ± 1.0 | J/mol*K | N/A | Finke H.L., 1981 | Close value of S(298.15 K)=298.6(1.7) J/mol*K was calculated by [ Andreevskii D.N., 1983] using other value for the entropy of the liquid state.; GT |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
87.40 | 298.15 | Andreevskii D.N., 1976 | GT |
87.99 | 300. | ||
118.41 | 400. | ||
144.98 | 500. | ||
166.90 | 600. | ||
185.06 | 700. | ||
200.29 | 800. | ||
213.22 | 900. | ||
224.26 | 1000. |
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
C5H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1620. ± 21. | kJ/mol | G+TS | Guo and Kass, 1992 | gas phase; Between H2O, MeOH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1586. ± 21. | kJ/mol | IMRB | Guo and Kass, 1992 | gas phase; Between H2O, MeOH; B |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -123.1 ± 0.3 | kJ/mol | Chyd | Turner, Goebel, et al., 1968 | liquid phase; solvent: Acetic acid; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 as indicated in comments:
B - John E. Bartmess
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 C5H8+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.19 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.14 ± 0.08 | EI | Puttemans and Delvaux, 1973 | LLK |
9.12 | PE | Demeo and Yencha, 1970 | RDSH |
9.16 ± 0.02 | PI | Demeo and El-Sayed, 1970 | RDSH |
9.35 | PE | Wiberg, Ellison, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 14.09 ± 0.15 | C2H4+H | EI | Puttemans and Delvaux, 1973 | LLK |
C3H4+ | 11.71 ± 0.10 | C2H4 | EI | Puttemans and Delvaux, 1973 | LLK |
C4H5+ | 11.23 ± 0.08 | CH3 | EI | Puttemans and Delvaux, 1973 | LLK |
C5H7+ | 10.64 ± 0.10 | H | EI | Puttemans and Delvaux, 1973 | LLK |
De-protonation reactions
C5H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1620. ± 21. | kJ/mol | G+TS | Guo and Kass, 1992 | gas phase; Between H2O, MeOH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1586. ± 21. | kJ/mol | IMRB | Guo and Kass, 1992 | gas phase; Between H2O, MeOH; B |
References
Go To: Top, Gas 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.
Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R.,
Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld,
Chem. Ber., 1991, 124, 2499-2521. [all data]
Good, Moore, et al., 1974
Good, W.D.; Moore, R.T.; Osborn, A.G.; Douslin, D.R.,
The enthalpies of formation of ethylcyclobutane, methylenecyclobutane, and 1,1-dimethylcyclopropane,
J. Chem. Thermodyn., 1974, 6, 303-310. [all data]
Finke H.L., 1981
Finke H.L.,
Thermodynamic properties of cyclopropylamine, cyclopentylamine, and methylenecyclobutane,
J. Chem. Thermodyn., 1981, 13, 345-355. [all data]
Andreevskii D.N., 1983
Andreevskii D.N.,
Value of the S(298.15) entropy of methylenecyclobutane in the gaseous state,
Zh. Fiz. Khim., 1983, 57, 2109. [all data]
Andreevskii D.N., 1976
Andreevskii D.N.,
The similar structures method in thermodynamics of C3-C5 methylenecycloalkanes,
Zh. Strukt. Khim., 1976, 17, 51-57. [all data]
Guo and Kass, 1992
Guo, H.Z.; Kass, S.R.,
Vinylcyclopropyl Anion - Structure, Reactivity, Thermodynamic Properties, and an Unusual Rearrangement,
J. Am. Chem. Soc., 1992, 114, 4, 1244, https://doi.org/10.1021/ja00030a019
. [all data]
Turner, Goebel, et al., 1968
Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M.,
Heats of hydrogenation. VIII. Compounds with three- and four-membered rings,
J. Am. Chem. Soc., 1968, 90, 4315-4322. [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]
Puttemans and Delvaux, 1973
Puttemans, J.-P.; Delvaux, J.C.,
Ionisation et fragmentation d'isomeres C5H8 sous impact electronique. Spiropentane - methylenecyclobutane - isoprene,
Ing. Chim. Brussell, 1973, 55(267-8), 7. [all data]
Demeo and Yencha, 1970
Demeo, D.A.; Yencha, A.J.,
Photoelectron spectra of bicyclic and exocyclic olefins,
J. Chem. Phys., 1970, 53, 4536. [all data]
Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A.,
Ionization potential and structure of olefins,
J. Chem. Phys., 1970, 52, 2622. [all data]
Wiberg, Ellison, et al., 1976
Wiberg, K.B.; Ellison, G.B.; Wendoloski, J.J.; Brundle, C.R.; Kuebler, N.A.,
Electronic states of organic molecules. 3. Photoelectron spectra of cycloalkenes and methylenecycloalkanes,
J. Am. Chem. Soc., 1976, 98, 7179. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas S°gas Entropy of gas at standard conditions ΔfH°gas Enthalpy of formation of gas 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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