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
Δfgas25.4kcal/molChydRoth, Adamczak, et al., 1991ALS
Δfgas29.05 ± 0.17kcal/molCcbGood, Moore, et al., 1974ALS
Quantity Value Units Method Reference Comment
gas71.44 ± 0.24cal/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 (cal/mol*K) Temperature (K) Reference Comment
20.89298.15Andreevskii D.N., 1976GT
21.03300.
28.301400.
34.651500.
39.890600.
44.230700.
47.870800.
50.961900.
53.5991000.

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
Δfliquid22.43 ± 0.14kcal/molCcbGood, Moore, et al., 1974ALS
Quantity Value Units Method Reference Comment
Δcliquid-765.95 ± 0.12kcal/molCcbGood, Moore, et al., 1974Corresponding Δfliquid = 22.43 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid50.24cal/mol*KN/AFinke, Messerly, et al., 1981DH
liquid50.33cal/mol*KN/ALebedev, Tsvetkova, et al., 1978DH
liquid50.33cal/mol*KN/ALebedev, Tsvetkova, et al., 1978, 2DH
liquid50.33cal/mol*KN/ALebedev, Lebedev, et al., 1975DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
31.33298.15Finke, Messerly, et al., 1981T = 12 to 301 K. Equation also given for temperature range 146 to 301 K.; DH
31.93298.15Lebedev, Tsvetkova, et al., 1978T = 12 to 315 K.; DH
31.93298.15Lebedev, Tsvetkova, et al., 1978, 2T = 12 to 315 K.; DH
31.93298.15Lebedev, Lebedev, et al., 1975T = 6 to 320 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

C5H7- + Hydrogen cation = Cyclobutane, methylene-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Δr387.1 ± 5.1kcal/molG+TSGuo and Kass, 1992gas phase; Between H2O, MeOH; B
Quantity Value Units Method Reference Comment
Δr379.0 ± 5.0kcal/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-29.43 ± 0.06kcal/molChydTurner, Goebel, et al., 1968liquid phase; solvent: Acetic acid; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]

Finke, Messerly, et al., 1981
Finke, H.L.; Messerly, J.F.; Lee-Bechtold, S.H., Thermodynamic properties of cyclopropylamine, cyclopentylamine, and methylenecyclobutane, J. Chem. Thermodyn., 1981, 13, 345-355. [all data]

Lebedev, Tsvetkova, et al., 1978
Lebedev, B.V.; Tsvetkova, L.Ya.; Rabinovich, I.B.; Finkel'shtein, E.Sh.; Strel'chik, B.S., Thermodynamic characteristics of methylenecyclobutane, Termodin. Org. Soedin., 1978, (7), 3-7. [all data]

Lebedev, Tsvetkova, et al., 1978, 2
Lebedev, B.V.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of methylenecyclobutane, J. Chem. Thermodyn., 1978, 10, 809-815. [all data]

Lebedev, Lebedev, et al., 1975
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, Y.G.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of methylenecyclobutane and 1,5-cyclooctadiene, Quatrieme Conference International de Thermodynamique Chimique, 1975, II, Thermophysique (capacites thermiques) pp. [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]


Notes

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