Cyclobutane, methylene-

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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

C5H7- + Hydrogen cation = Cyclobutane, methylene-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Δr387.1 ± 5.1kcal/molG+TSGuo and Kass, 1992gas phase; Between H2O, MeOH; B
Quantity Value Units Method Reference Comment
Δr379.0 ± 5.0kcal/molIMRBGuo and Kass, 1992gas phase; Between H2O, MeOH; B

Cyclobutane, methylene- + Hydrogen = Cyclobutane, methyl-

By formula: C5H8 + H2 = C5H10

Quantity Value Units Method Reference Comment
Δr-29.43 ± 0.06kcal/molChydTurner, Goebel, et al., 1968liquid phase; solvent: Acetic acid; ALS

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 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 C5H8+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.19 ± 0.02PEBieri, Burger, et al., 1977LLK
9.14 ± 0.08EIPuttemans and Delvaux, 1973LLK
9.12PEDemeo and Yencha, 1970RDSH
9.16 ± 0.02PIDemeo and El-Sayed, 1970RDSH
9.35PEWiberg, Ellison, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+14.09 ± 0.15C2H4+HEIPuttemans and Delvaux, 1973LLK
C3H4+11.71 ± 0.10C2H4EIPuttemans and Delvaux, 1973LLK
C4H5+11.23 ± 0.08CH3EIPuttemans and Delvaux, 1973LLK
C5H7+10.64 ± 0.10HEIPuttemans and Delvaux, 1973LLK

De-protonation reactions

C5H7- + Hydrogen cation = Cyclobutane, methylene-

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Δr387.1 ± 5.1kcal/molG+TSGuo and Kass, 1992gas phase; Between H2O, MeOH; B
Quantity Value Units Method Reference Comment
Δr379.0 ± 5.0kcal/molIMRBGuo and Kass, 1992gas phase; Between H2O, MeOH; B

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-IW-1088
NIST MS number 227746

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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-127.536.Heberger, 199025. m/0.25 mm/0.50 μm, He
CapillaryOV-130.546.Heberger, 199025. m/0.25 mm/0.50 μm, He
PackedSqualane27.534.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.536.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.537.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.539.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryPetrocol DH535.White, Hackett, et al., 1992100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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]

Turner, Goebel, et al., 1968
Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M., Heats of hydrogenation. VIII. Compounds with three- and four-membered rings, J. Am. Chem. Soc., 1968, 90, 4315-4322. [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]

Puttemans and Delvaux, 1973
Puttemans, J.-P.; Delvaux, J.C., Ionisation et fragmentation d'isomeres C5H8 sous impact electronique. Spiropentane - methylenecyclobutane - isoprene, Ing. Chim. Brussell, 1973, 55(267-8), 7. [all data]

Demeo and Yencha, 1970
Demeo, D.A.; Yencha, A.J., Photoelectron spectra of bicyclic and exocyclic olefins, J. Chem. Phys., 1970, 53, 4536. [all data]

Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A., Ionization potential and structure of olefins, J. Chem. Phys., 1970, 52, 2622. [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]

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]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References