Cyclopropane,ethenyl-

• Formula: C₅H₈
• Molecular weight: 68.1170
• IUPAC Standard InChI: InChI=1S/C5H8/c1-2-5-3-4-5/h2,5H,1,3-4H2 Copy

  
• IUPAC Standard InChIKey: YIWFBNMYFYINAD-UHFFFAOYSA-N Copy
• CAS Registry Number: 693-86-7
• 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.
• Other names: Ethenylcyclopropane
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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:
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

Enthalpy of vaporization

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

 +  =

By formula: C₅H₇^- + H⁺ = C₅H₈

2 +  =

By formula: 2H₂ + C₅H₈ = C₅H₁₂

 +  =

By formula: H₂ + C₅H₈ = C₅H₁₀

=

By formula: C₅H₈ = C₅H₈

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:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₅H₈⁺ (ion structure unspecified)

Ionization energy determinations

De-protonation reactions

 +  =

By formula: C₅H₇^- + H⁺ = C₅H₈

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

View large format table.

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes

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

Lebedeva, Gutner, et al., 1977
Lebedeva, N.D.; Gutner, N.M.; Nazarova, L.F., Enthalpies of burning and the formation of some substituted derivatives of cyclopropane, Termodin. Org. Soedin., 1977, 26-29. [all data]

Fierens and Nasielski, 1962
Fierens, P.J.C.; Nasielski, J., Chaleurs de combustion de derives cyclopropaniques et pouvoir de conjugaison du groupe cyclopropyle, Bull. Soc. Chim. Belg., 1962, 71, 187-202. [all data]

Slabey, 1952
Slabey, V.A., Dehydration of methylcyclopropylcarbinol over alumina. A synthesis of vinylcyclopropane, J. Am. Chem. Soc., 1952, 74, 4930-4932. [all data]

Anonymous, 1949
Anonymous, R., , Am. Pet. Inst. Res. Proj. 45, Ohio State Univ., 1949. [all data]

Van Volkenburgh, Greenlee, et al., 1949
Van Volkenburgh, R.; Greenlee, K.W.; Derfer, J.M.; Boord, C.E., A Synthesis of Vinylcyclopropane, J. Am. Chem. Soc., 1949, 71, 3595. [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]

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]

Roth, Kirmse, et al., 1982
Roth, W.R.; Kirmse, W.; Hoffmann, W.; Lennartz, H.W., Heats of hydrogenation. III. Effect of fluoro substituents on the thermal rearrangement of cyclopropane systems, Chem. Ber., 1982, 115, 2508-2515. [all data]

Chesick, 1963
Chesick, J.P., Kinetics of the thermal interconversion of 2-methylmethylenecyclopropane and ethylidenecyclopropane, J. Am. Chem. Soc., 1963, 85, 2720-2723. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Harada, Seki, et al., 1973
Harada, Y.; Seki, K.; Suzuki, A.; Inokuchi, H., Photoelectron spectrum of vinylcyclopropane, Chem. Lett., 1973, 893. [all data]

Bruckmann and Klessinger, 1974
Bruckmann, P.; Klessinger, M., Photoelektronenspektren organischer verbindungen. V. Wechselwirkung kleiner ringe mit π-systemen, Chem. Ber., 1974, 107, 1108. [all data]

Gleiter, Heilbronner, et al., 1971
Gleiter, R.; Heilbronner, E.; de Meijere, A., Die konjugative Wechselwirkung zwischen π-und Walsh-Orbitalen: das Photoelektron-Spektrum des Homofulvens, Helv. Chim. Acta, 1971, 54, 1029. [all data]

Askani, Gleiter, et al., 1971
Askani, R.; Gleiter, R.; Heilbronner, E.; Hornung, V.; Musso, H., The orbital sequence in semibullvalene, barbaralene and dihydrobullvalene, Tetrahedron Lett., 1971, 4461. [all data]

Heberger, 1990
Heberger, K., Identification of C₅H₈ Isomers Through Reactions of Singlet Methylene, CH₂(ã¹A₁), with Unsaturated Hydrocarbons Using Capillary Gas Chromatography - Mass Spectrometry, Analyst, 1990, 115, 6, 725-729, https://doi.org/10.1039/an9901500725 . [all data]

Schomburg and Dielmann, 1973
Schomburg, G.; Dielmann, G., Use of retention increments for identification and correlation of saturated and unsaturated cyclopropane hydrocarbons by means of Kovats indices, Anal. Chem., 1973, 45, 9, 1647-1658, https://doi.org/10.1021/ac60331a021 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  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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