Cyclobutane, methylene-

• Formula: C₅H₈
• Molecular weight: 68.1170
• IUPAC Standard InChI: InChI=1S/C5H8/c1-5-3-2-4-5/h1-4H2 Copy

  
• IUPAC Standard InChIKey: QIRVGKYPAOQVNP-UHFFFAOYSA-N Copy
• 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:
  • Cyclobutane, methylene-
• Other names: Methylenecyclobutane
• Information on this page:
  • Phase change data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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Phase change 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:
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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Slabey, 1946
Slabey, V.A., J. Am. Chem. Soc., 1946, 68, 1335. [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. [all data]

Lebedev, Tsvetkova, et al., 1978
Lebedev, B.V.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of methylenecyclobutane, J. Chem. Thermodyn., 1978, 10, 809-15. [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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

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, Tsvetkova, et al., 1978, 3
Lebedev, B.V.; Tsvetkova, L.Y.; Rabinovich, I.B.; Finkel'shtein, E.S.; Strel'chick, B.S., Termodin. Org. Soedin., 1978, 7, 3. [all data]

Lebedev, Tsvetkova, et al., 1978, 4
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, 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]

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]

Finke, Messerly, et al., 1981, 2
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]

Notes

Go To: Top, Phase change data, References

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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