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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Options:
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 2.43 | kcal/mol | Chyd | Allinger, Dodziuk, et al., 1982 | ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
24.410 | 298.15 | Andreevskii D.N., 1976 | GT |
24.579 | 300. | ||
33.681 | 400. | ||
41.730 | 500. | ||
48.430 | 600. | ||
54.001 | 700. | ||
58.681 | 800. | ||
62.641 | 900. | ||
66.021 | 1000. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -4.82 ± 0.21 | kcal/mol | Ccb | Labbauf and Rossini, 1961 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -901.08 ± 0.19 | kcal/mol | Ccb | Labbauf and Rossini, 1961 | Corresponding ΔfHºliquid = -4.80 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 349. ± 4. | K | AVG | N/A | Average of 14 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 145.32 | K | N/A | Anonymous, 1958 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 146.0 | K | N/A | Anonymous, 1958 | Uncertainty assigned by TRC = 0.15 K; TRC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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° | -27.70 ± 0.23 | kcal/mol | Chyd | Allinger, Dodziuk, et al., 1982 | liquid phase; solvent: Hexane |
ΔrH° | -26.88 ± 0.02 | kcal/mol | Chyd | Turner and Garner, 1958 | liquid phase; solvent: Acetic acid |
ΔrH° | -26.85 ± 0.05 | kcal/mol | Chyd | Turner and Garner, 1957 | liquid phase; solvent: Acetic acid |
ΔrH° | -26.82 ± 0.08 | kcal/mol | Chyd | Turner and Garner, 1957, 2 | liquid phase; solvent: Acetic acid |
By formula: C6H10 = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 3.78 ± 0.20 | kcal/mol | Eqk | Yursha and Kabo, 1975 | gas phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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) | 198.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 192.0 | kcal/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
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, NIST Free Links, NIST Subscription Links, 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
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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-NW-6766 |
NIST MS number | 238669 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), NIST Free Links, NIST Subscription Links, 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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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]
Andreevskii D.N., 1976
Andreevskii D.N.,
The similar structures method in thermodynamics of C3-C5 methylenecycloalkanes,
Zh. Strukt. Khim., 1976, 17, 51-57. [all data]
Labbauf and Rossini, 1961
Labbauf, A.; Rossini, F.D.,
Heats of combustion, formation, and hydrogenation of 14 selected cyclomonoolefin hydrocarbons,
J. Phys. Chem., 1961, 65, 476-480. [all data]
Anonymous, 1958
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Ohio State Univ., 1958. [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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.