Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

NOTICE: Due to scheduled maintenance at our Gaithersburg campus, this site will not be available from 5:00 pm EDT (21:00 UTC) on Friday October 25 until 5:00 pm (21:00 UTC) on Sunday October 27. We apologize for any inconvenience this outage may cause.

Cyclopentane, methylene-

Data at NIST subscription sites:

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, Condensed 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 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
Deltafgas10.2kJ/molChydAllinger, Dodziuk, et al., 1982ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
102.13298.15Andreevskii D.N., 1976GT
102.84300.
140.92400.
174.60500.
202.63600.
225.94700.
245.52800.
262.09900.
276.231000.

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), 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
Deltafliquid-20.2 ± 0.88kJ/molCcbLabbauf and Rossini, 1961 
Quantity Value Units Method Reference Comment
Deltacliquid-3770.1 ± 0.79kJ/molCcbLabbauf and Rossini, 1961Corresponding «DELTA»fliquid = -20.1 kJ/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), 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
Tboil349. ± 4.KAVGN/AAverage of 14 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus145.32KN/AAnonymous, 1958Uncertainty assigned by TRC = 0.5 K; TRC
Tfus146.0KN/AAnonymous, 1958Uncertainty assigned by TRC = 0.15 K; TRC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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), 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

Hydrogen + Cyclopentane, methylene- = Cyclopentane, methyl-

By formula: H2 + C6H10 = C6H12

Quantity Value Units Method Reference Comment
Deltar-115.9 ± 0.96kJ/molChydAllinger, Dodziuk, et al., 1982liquid phase; solvent: Hexane
Deltar-112.5 ± 0.08kJ/molChydTurner and Garner, 1958liquid phase; solvent: Acetic acid
Deltar-112.3 ± 0.2kJ/molChydTurner and Garner, 1957liquid phase; solvent: Acetic acid
Deltar-112.2 ± 0.3kJ/molChydTurner and Garner, 1957, 2liquid phase; solvent: Acetic acid

Cyclopentene, 1-methyl- = Cyclopentane, methylene-

By formula: C6H10 = C6H10

Quantity Value Units Method Reference Comment
Deltar15.8 ± 0.84kJ/molEqkYursha and Kabo, 1975gas 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), 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)832.4kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity803.5kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.70 ± 0.05EIWolkoff and Holmes, 1979LLK
8.96 ± 0.02PEBieri, Burger, et al., 1977LLK
7.2EIShikhmamedbekova, Aslanov, et al., 1970RDSH
9.26 ± 0.05EIPraet, 1970RDSH
8.55 ± 0.01PIPraet, 1970RDSH
8.51 ± 0.01PEPraet and Delwiche, 1970RDSH
8.94 ± 0.01PIDemeo and El-Sayed, 1970RDSH
9.05 ± 0.02EIWinters and Collins, 1969RDSH
9.14PEWiberg, Ellison, et al., 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.44 ± 0.20?EIWinters and Collins, 1969RDSH
C3H5+10.2C3H5EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C3H5+14.05 ± 0.05C3H5EIPraet, 1970RDSH
C3H5+12.03 ± 0.13?EIWinters and Collins, 1969RDSH
C4H5+9.7C2H5EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C4H5+12.69 ± 0.17?EIWinters and Collins, 1969RDSH
C4H6+10.2C2H4EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C4H6+12.32 ± 0.05C2H4EIPraet, 1970RDSH
C4H6+10.88 ± 0.07?EIWinters and Collins, 1969RDSH
C5H5+13.45 ± 0.19?EIWinters and Collins, 1969RDSH
C5H7+10.02 ± 0.05CH3EIWolkoff and Holmes, 1979LLK
C5H7+8.2CH3EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C5H7+11.71 ± 0.05CH3EIPraet, 1970RDSH
C5H7+9.65 ± 0.03CH3EIWinters and Collins, 1969RDSH
C5H8+9.2CH2EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C6H7+11.66 ± 0.16H2+HEIWinters and Collins, 1969RDSH
C6H8+8.7H2EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C6H9+12.13 ± 0.05HEIPraet, 1970RDSH
C6H9+10.20 ± 0.03HEIWinters and Collins, 1969RDSH

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, 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.

Mass spectrum
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

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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), 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]


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), References