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Cyclobutene

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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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C4H6+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.43 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)784.4kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity753.6kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.43 ± 0.02PEBieri, Burger, et al., 1977LLK
9.43PEBischof and Heilbronner, 1970RDSH
9.59PEWiberg, Ellison, et al., 1976Vertical value; LLK
9.43 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK
9.43PEClary, Lewis, et al., 1974Vertical value; LLK

De-protonation reactions

cyclobutene-1-ide anion + Hydrogen cation = Cyclobutene

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Deltar1693. ± 6.3kJ/molCIDCTian, Fattahi, et al., 2006gas phase; B
Deltar1661. ± 21.kJ/molG+TSKass, Filley, et al., 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar1659. ± 6.7kJ/molH-TSTian, Fattahi, et al., 2006gas phase; B
Deltar1628. ± 21.kJ/molIMRBKass, Filley, et al., 1986gas phase; B

References

Go To: Top, 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.

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]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Bischof and Heilbronner, 1970
Bischof, P.; Heilbronner, E., Photoelektron-Spektren von Cycloalkenen und Cycloalkadienen, Helv. Chim. Acta, 1970, 53, 1677. [all data]

Wiberg, Ellison, et al., 1976
Wiberg, K.B.; Ellison, G.B.; Wendoloski, J.J.; Brundle, C.R.; Kuebler, N.A., Electronic states of organic molecules. 3. Photoelectron spectra of cycloalkenes and methylenecycloalkanes, J. Am. Chem. Soc., 1976, 98, 7179. [all data]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the 2A<--2X and 2B<--2X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

Clary, Lewis, et al., 1974
Clary, D.C.; Lewis, A.A.; Morland, D.; Murrell, J.N.; Heilbronner, E., Ionization potentials of cycloalkenes, J. Chem. Soc. Faraday Trans. 2, 1974, 70, 1889. [all data]

Tian, Fattahi, et al., 2006
Tian, Z.X.; Fattahi, A.; Lis, L.; Kass, S.R., Cycloalkane and cycloalkene C-H bond dissociation energies, J. Am. Chem. Soc., 2006, 128, 51, 17087-17092, https://doi.org/10.1021/ja065348u . [all data]

Kass, Filley, et al., 1986
Kass, S.R.; Filley, J.; Van Doren, J.M.; DePuy, C.H., Nitrous oxide in gas-phase ion-molecule chemistry: A versatile reagent for the determination of carbanion structure, J. Am. Chem. Soc., 1986, 108, 2849. [all data]


Notes

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