Cyclopentane, methylene-

• Formula: C₆H₁₀
• Molecular weight: 82.1436
• IUPAC Standard InChI: InChI=1S/C6H10/c1-6-4-2-3-5-6/h1-5H2 Copy

  
• IUPAC Standard InChIKey: NFJPEKRRHIYYES-UHFFFAOYSA-N Copy
• 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:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Phase change data, Reaction thermochemistry data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Phase change data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, 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 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

=

By formula: C₆H₁₀ = C₆H₁₀

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry 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 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)

Ionization energy determinations

Appearance energy determinations

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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: 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.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

Gas Chromatography

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

View large format table.

Normal alkane RI, non-polar column, custom temperature program

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Phase change data, 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.

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]

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, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas 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.