Cyclopentane, methylene-
- Formula: C6H10
- Molecular weight: 82.1436
- IUPAC Standard InChIKey: NFJPEKRRHIYYES-UHFFFAOYSA-N
- CAS Registry Number: 1528-30-9
- 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: Methylenecyclopentane; 1-Methylenecyclopentane
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, 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 by: 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: H2 + C6H10 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -115.9 ± 0.96 | kJ/mol | Chyd | Allinger, Dodziuk, et al., 1982 | liquid phase; solvent: Hexane |
ΔrH° | -112.5 ± 0.08 | kJ/mol | Chyd | Turner and Garner, 1958 | liquid phase; solvent: Acetic acid |
ΔrH° | -112.3 ± 0.2 | kJ/mol | Chyd | Turner and Garner, 1957 | liquid phase; solvent: Acetic acid |
ΔrH° | -112.2 ± 0.3 | kJ/mol | Chyd | Turner and Garner, 1957, 2 | liquid phase; solvent: Acetic acid |
By formula: C6H10 = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.8 ± 0.84 | kJ/mol | Eqk | Yursha and Kabo, 1975 | gas phase |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
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 C6H10+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 832.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 803.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.70 ± 0.05 | EI | Wolkoff and Holmes, 1979 | LLK |
8.96 ± 0.02 | PE | Bieri, Burger, et al., 1977 | LLK |
7.2 | EI | Shikhmamedbekova, Aslanov, et al., 1970 | RDSH |
9.26 ± 0.05 | EI | Praet, 1970 | RDSH |
8.55 ± 0.01 | PI | Praet, 1970 | RDSH |
8.51 ± 0.01 | PE | Praet and Delwiche, 1970 | RDSH |
8.94 ± 0.01 | PI | Demeo and El-Sayed, 1970 | RDSH |
9.05 ± 0.02 | EI | Winters and Collins, 1969 | RDSH |
9.14 | PE | Wiberg, Ellison, et al., 1976 | Vertical value; LLK |
Appearance energy determinations
Gas Chromatography
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
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-101 | 100. | 657. | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | OV-101 | 80. | 654. | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | BP-1 | 100. | 657. | Bermejo, Blanco, et al., 1987 | N2; Column length: 12. m; Column diameter: 0.22 mm |
Capillary | BP-1 | 80. | 654. | Bermejo, Blanco, et al., 1987 | N2; Column length: 12. m; Column diameter: 0.22 mm |
Capillary | OV-101 | 100. | 657. | Bermejo, Blanco, et al., 1987 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | OV-101 | 80. | 654. | Bermejo, Blanco, et al., 1987 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | Squalane | 50. | 650. | Schomburg, 1966 |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 650. | Chen, 2008 | Program: not specified |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Allinger, Dodziuk, et al., 1982
Allinger, N.L.; Dodziuk, H.; Rogers, D.W.; Naik, S.N.,
Heats of hydrogenation and formation of some 5-membered ring compounds by molecular mechanics calculations and direct measurements,
Tetrahedron, 1982, 38, 1593-1597. [all data]
Turner and Garner, 1958
Turner, R.B.; Garner, R.H.,
Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs,
J. Am. Chem. Soc., 1958, 80, 1424-1430. [all data]
Turner and Garner, 1957
Turner, R.B.; Garner, R.H.,
Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs,
J. Am. Chem. Soc., 1957, 80, 1424-1430. [all data]
Turner and Garner, 1957, 2
Turner, R.B.; Garner, R.H.,
The stability relationship of 1-methyl-cyclopentene and methylenecyclopentane,
J. Am. Chem. Soc., 1957, 79, 253. [all data]
Yursha and Kabo, 1975
Yursha, I.A.; Kabo, G.Ya.,
Thermodynamics of the isomerisation of methylcyclopentines,
Russ. J. Phys. Chem. (Engl. Transl.), 1975, 49, 765-766. [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]
Wolkoff and Holmes, 1979
Wolkoff, P.; Holmes, J.L.,
Isomeric cyclic [C6H10]+ ions. The energy barrier to ring opening,
Can. J. Chem., 1979, 57, 348. [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]
Shikhmamedbekova, Aslanov, et al., 1970
Shikhmamedbekova, A.Z.; Aslanov, F.A.; Gadzhiev, M.M.; Gulamova, T.E.; Akhmedova, F.N.,
Mass spectrometric study of methylene cycloalkenes,
Dokl. Phys. Chem., 1970, 26, 34. [all data]
Praet, 1970
Praet, M.-Th.,
Ionisation et dissociation du 1-methyl-cyclopentene, du methylenecyclopentane et de quelques isomeres par impact d'electrons et de photons,
Org. Mass Spectrom., 1970, 4, 65. [all data]
Praet and Delwiche, 1970
Praet, M.-T.; Delwiche, J.,
Ionization energies of some cyclic molecules,
Chem. Phys. Lett., 1970, 5, 546. [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]
Winters and Collins, 1969
Winters, R.E.; Collins, J.H.,
Mass spectrometric studies of structural isomers. II.Mono- and bicyclic C6H10 molecules,
Org. Mass Spectrom., 1969, 2, 299. [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]
Diez, Guillen, et al., 1990
Diez, M.A.; Guillen, M.D.; Blanco, C.G.; Bermejo, J.,
Chromatographic study of methylcyclopentadiene dimers and iso-dimers and determination of their boiling points,
J. Chromatogr., 1990, 508, 363-374, https://doi.org/10.1016/S0021-9673(00)91279-2
. [all data]
Bermejo, Blanco, et al., 1987
Bermejo, J.; Blanco, C.G.; Diez, M.A.; Guillén, M.D.,
Kováts retention indices of selected mono and polycyclic olefins,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1987, 10, 8, 461-463, https://doi.org/10.1002/jhrc.1240100809
. [all data]
Schomburg, 1966
Schomburg, G.,
Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe,
J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4
. [all data]
Chen, 2008
Chen, H.-F.,
Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression,
Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003
. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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