Cyclobutane, methylene-
- Formula: C5H8
- Molecular weight: 68.1170
- IUPAC Standard InChIKey: QIRVGKYPAOQVNP-UHFFFAOYSA-N
- CAS Registry Number: 1120-56-5
- 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. - Species with the same structure:
- Other names: Methylenecyclobutane
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
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- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 387.1 ± 5.1 | kcal/mol | G+TS | Guo and Kass, 1992 | gas phase; Between H2O, MeOH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 379.0 ± 5.0 | kcal/mol | IMRB | Guo and Kass, 1992 | gas phase; Between H2O, MeOH; B |
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -29.43 ± 0.06 | kcal/mol | Chyd | Turner, Goebel, et al., 1968 | liquid 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 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
9.14 ± 0.08 | EI | Puttemans and Delvaux, 1973 | LLK |
9.12 | PE | Demeo and Yencha, 1970 | RDSH |
9.16 ± 0.02 | PI | Demeo and El-Sayed, 1970 | RDSH |
9.35 | PE | Wiberg, Ellison, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 14.09 ± 0.15 | C2H4+H | EI | Puttemans and Delvaux, 1973 | LLK |
C3H4+ | 11.71 ± 0.10 | C2H4 | EI | Puttemans and Delvaux, 1973 | LLK |
C4H5+ | 11.23 ± 0.08 | CH3 | EI | Puttemans and Delvaux, 1973 | LLK |
C5H7+ | 10.64 ± 0.10 | H | EI | Puttemans and Delvaux, 1973 | LLK |
De-protonation reactions
C5H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 387.1 ± 5.1 | kcal/mol | G+TS | Guo and Kass, 1992 | gas phase; Between H2O, MeOH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 379.0 ± 5.0 | kcal/mol | IMRB | Guo and Kass, 1992 | gas 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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Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-1 | 27. | 536. | Heberger, 1990 | 25. m/0.25 mm/0.50 μm, He |
Capillary | OV-1 | 30. | 546. | Heberger, 1990 | 25. m/0.25 mm/0.50 μm, He |
Packed | Squalane | 27. | 534. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 536. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 537. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 539. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH | 535. | White, Hackett, et al., 1992 | 100. 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, 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]
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
- Symbols used in this document:
AE Appearance energy 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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