Cyclopentene, 4-methyl-
- Formula: C6H10
- Molecular weight: 82.1436
- IUPAC Standard InChI: InChI=1S/C6H10/c1-6-4-2-3-5-6/h2-3,6H,4-5H2,1H3
- IUPAC Standard InChIKey: FWMRUAODTCVEQK-UHFFFAOYSA-N
- CAS Registry Number: 1759-81-5
- 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: 1-Methyl-3-cyclopentene; 4-Methylcyclopentene; 4-Methyl-1-cyclopentene
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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 |
|---|---|---|---|---|---|
| ΔfH°gas | 15. ± 2. | kJ/mol | Ccb | Labbauf and Rossini, 1961 | Heat 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -17.7 ± 1.0 | kJ/mol | Ccb | Labbauf and Rossini, 1961 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3772.6 ± 1.0 | kJ/mol | Ccb | Labbauf and Rossini, 1961 | Corresponding ΔfHºliquid = -17.6 kJ/mol (simple calculation by NIST; no Washburn corrections) |
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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 348.7 | K | N/A | Anonymous, 1951 | Uncertainty assigned by TRC = 1.5 K; TRC |
| Tboil | 338.3 | K | N/A | Cook, 1949 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Tboil | 348. | K | N/A | Mousseron, 1946 | Uncertainty assigned by TRC = 6. K; TRC |
| Tboil | 345.2 | K | N/A | Zelinskii, 1902 | Uncertainty assigned by TRC = 4. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 146.06 | K | N/A | Anonymous, 1951 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 32. ± 2. | kJ/mol | V | Labbauf and Rossini, 1961 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
| ΔvapH° | 32.7 | kJ/mol | N/A | Labbauf and Rossini, 1961 | DRB |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 33.2 | 286. | A | Stephenson and Malanowski, 1987 | Based on data from 271. to 403. K. See also Dykyj, 1972.; AC |
Reaction 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
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: C6H10 = C6H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 7.5 ± 0.2 | kJ/mol | Eqk | Yursha and Kabo, 1975 | gas phase |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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| 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 | R.F.KENDALL BUR. MINES, U.S. DEPT. INT., BARTLESVILLE, OKLA |
| NIST MS number | 19270 |
Gas Chromatography
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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: 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 | Squalane | 50. | 610. | Bogoslovsky, Anvaer, et al., 1978 | |
| Capillary | Squalane | 50. | 610. | Schomburg, 1966 |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 611. | Ramnas, Ostermark, et al., 1994 | 50. m/0.32 mm/1.0 μm, He, 2. K/min; Tstart: -20. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Squalane | 610. | Chen, 2008 | Program: not specified |
References
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, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Anonymous, 1951
Anonymous, R.,
, Sunbury Rep. No. 4199, Anglo-Iranian Oil Co., 1951. [all data]
Cook, 1949
Cook, N.C.,
Penn. State Univ., 1949. [all data]
Mousseron, 1946
Mousseron, M.,
Bull. Soc. Chim. Fr., 1946, 1946, 218. [all data]
Zelinskii, 1902
Zelinskii, N.D.,
Optically active hydrocarbons in the cyclopentene and cyclohexene series,
Ber. Dtsch. Chem. Ges., 1902, 35, 2488. [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]
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]
Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S.,
Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [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]
Ramnas, Ostermark, et al., 1994
Ramnas, O.; Ostermark, U.; Peterson, G.,
Characterization of sixty alkenes in a cat-cracked gasoline naphtha by gas chromatography,
Chromatographia, 1994, 38, 3/4, 222-226, https://doi.org/10.1007/BF02290340
. [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
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- Symbols used in this document:
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 ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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