Cyclobutane, methylene-

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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
Δfgas106.kJ/molChydRoth, Adamczak, et al., 1991ALS
Δfgas121.5 ± 0.71kJ/molCcbGood, Moore, et al., 1974ALS
Quantity Value Units Method Reference Comment
gas298.9 ± 1.0J/mol*KN/AFinke H.L., 1981Close 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
87.40298.15Andreevskii D.N., 1976GT
87.99300.
118.41400.
144.98500.
166.90600.
185.06700.
200.29800.
213.22900.
224.261000.

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- + Hydrogen cation = Cyclobutane, methylene-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Δr1620. ± 21.kJ/molG+TSGuo and Kass, 1992gas phase; Between H2O, MeOH; B
Quantity Value Units Method Reference Comment
Δr1586. ± 21.kJ/molIMRBGuo and Kass, 1992gas phase; Between H2O, MeOH; B

Cyclobutane, methylene- + Hydrogen = Cyclobutane, methyl-

By formula: C5H8 + H2 = C5H10

Quantity Value Units Method Reference Comment
Δr-123.1 ± 0.3kJ/molChydTurner, Goebel, et al., 1968liquid phase; solvent: Acetic acid; 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 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 ± 0.02PEBieri, Burger, et al., 1977LLK
9.14 ± 0.08EIPuttemans and Delvaux, 1973LLK
9.12PEDemeo and Yencha, 1970RDSH
9.16 ± 0.02PIDemeo and El-Sayed, 1970RDSH
9.35PEWiberg, Ellison, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+14.09 ± 0.15C2H4+HEIPuttemans and Delvaux, 1973LLK
C3H4+11.71 ± 0.10C2H4EIPuttemans and Delvaux, 1973LLK
C4H5+11.23 ± 0.08CH3EIPuttemans and Delvaux, 1973LLK
C5H7+10.64 ± 0.10HEIPuttemans and Delvaux, 1973LLK

De-protonation reactions

C5H7- + Hydrogen cation = Cyclobutane, methylene-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Δr1620. ± 21.kJ/molG+TSGuo and Kass, 1992gas phase; Between H2O, MeOH; B
Quantity Value Units Method Reference Comment
Δr1586. ± 21.kJ/molIMRBGuo and Kass, 1992gas 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

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