Cyclopentene, 3-methyl-

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Gas phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas9.67kJ/molChydAllinger, Dodziuk, et al., 1982 
Δfgas7.36 ± 0.71kJ/molCmFuchs and Peacock, 1979 
Δfgas8. ± 2.kJ/molCcbLabbauf and Rossini, 1961Heat of formation derived by Cox and Pilcher, 1970

Condensed phase thermochemistry 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid-24.9 ± 1.8kJ/molCcbLabbauf and Rossini, 1961Reanalyzed by Cox and Pilcher, 1970, Original value = -23.8 ± 0.63 kJ/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-3766.5 ± 0.54kJ/molCcbLabbauf and Rossini, 1961Corresponding Δfliquid = -23.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
152.3298.15Fuchs and Peacock, 1979DH

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tboil339. ± 3.KAVGN/AAverage of 12 values; Individual data points
Quantity Value Units Method Reference Comment
Δvap31.0 ± 0.3kJ/molCFuchs and Peacock, 1979ALS
Δvap31.0 ± 0.2kJ/molGCCFuchs and Peacock, 1979AC
Δvap32. ± 2.kJ/molVLabbauf and Rossini, 1961Heat of formation derived by Cox and Pilcher, 1970; ALS
Δvap32.9kJ/molN/ALabbauf and Rossini, 1961DRB

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
32.1278.AStephenson and Malanowski, 1987Based on data from 263. to 392. K. See also Dykyj, 1972.; AC

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:


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:
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

IE (eV) Method Reference Comment
8.95EILossing and Traeger, 1975LLK
8.95 ± 0.01PERang, Paldoia, et al., 1974LLK
8.99 ± 0.04EIWinters and Collins, 1969RDSH
8.98 ± 0.05PEMcAlduff, Caramella, et al., 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.24 ± 0.32?EIWinters and Collins, 1969RDSH
C3H5+12.28 ± 0.17?EIWinters and Collins, 1969RDSH
C4H5+12.69 ± 0.20?EIWinters and Collins, 1969RDSH
C4H6+10.69 ± 0.07?EIWinters and Collins, 1969RDSH
C5H5+13.35 ± 0.05?EIWinters and Collins, 1969RDSH
C5H7+8.95CH3EILossing and Traeger, 1975, 2LLK
C5H7+10.03CH3EILossing and Traeger, 1975LLK
C5H7+9.67 ± 0.11CH3EIWinters and Collins, 1969RDSH
C5H7+10.52CH3EIPignataro, Cassuto, et al., 1967RDSH
C6H7+11.75 ± 0.04H2+HEIWinters and Collins, 1969RDSH
C6H9+10.35 ± 0.17HEIWinters and Collins, 1969RDSH

References

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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]

Fuchs and Peacock, 1979
Fuchs, R.; Peacock, L.A., Heats of vaporization and gaseous heats of formation of some five- and six-membered ring alkenes, Can. J. Chem., 1979, 57, 2302-2304. [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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Lossing and Traeger, 1975
Lossing, F.P.; Traeger, J.C., Stabilization in cyclopentadienyl, cyclopentenyl, and cyclopentyl cations, J. Am. Chem. Soc., 1975, 97, 1579. [all data]

Rang, Paldoia, et al., 1974
Rang, S.; Paldoia, P.; Talvari, A., Ionization potentials of unsaturated hydrocarbons. 2. Mono-substituted cyclopentenes and cyclohexenes, Eesti. NSV Tead. Akad. Toim., 1974, 354. [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]

McAlduff, Caramella, et al., 1978
McAlduff, E.J.; Caramella, P.; Houk, K.N., Photoelectron spectra of 3-substituted cyclopentenes. Correlations between ionization potentials and cycloaddition regioselectivity, J. Am. Chem. Soc., 1978, 100, 105. [all data]

Lossing and Traeger, 1975, 2
Lossing, F.P.; Traeger, J.C., Free radicals by mass spectrometry XLVI. Heats of formation of C5H7 and C5H9 radicals and cations., J. Am. Chem. Soc., 1975, 19, 9. [all data]

Pignataro, Cassuto, et al., 1967
Pignataro, S.; Cassuto, A.; Lossing, F.P., Free radicals by mass spectrometry. XXXVI. Ionization potentials of conjugated and nonconjugated radicals, J. Am. Chem. Soc., 1967, 89, 3693. [all data]


Notes

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