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
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas Chromatography
• Data at other public NIST sites:
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  • Gas Phase Kinetics Database
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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

References

Go To: Top, 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.

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]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  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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