Cyclopropane,ethenyl-

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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)

Quantity Value Units Method Reference Comment
Proton affinity (review)816.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity787.5kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.7PEHarada, Seki, et al., 1973LLK
9.15PEBruckmann and Klessinger, 1974Vertical value; LLK
9.2PEGleiter, Heilbronner, et al., 1971Vertical value; LLK
9.1PEAskani, Gleiter, et al., 1971Vertical value; LLK

De-protonation reactions

1-vinylcyclopropanide anion + Hydrogen cation = Cyclopropane,ethenyl-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Δr1647. ± 13.kJ/molG+TSGuo and Kass, 1992gas phase; Between Me2NH, H2O; B
Quantity Value Units Method Reference Comment
Δr1617. ± 13.kJ/molIMRBGuo and Kass, 1992gas phase; Between Me2NH, H2O; B

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.

Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-130.536.Heberger, 199025. m/0.25 mm/0.50 μm, He
CapillarySqualane120.515.6Schomburg and Dielmann, 1973Column length: 100. m; Column diameter: 0.25 mm

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.

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]

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]

Heberger, 1990
Heberger, K., Identification of C5H8 Isomers Through Reactions of Singlet Methylene, CH21A1), 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

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