Cyclopentene, 1-methyl-

Formula: C₆H₁₀
Molecular weight: 82.1436
IUPAC Standard InChI: InChI=1S/C6H10/c1-6-4-2-3-5-6/h4H,2-3,5H2,1H3
IUPAC Standard InChIKey: ATQUFXWBVZUTKO-UHFFFAOYSA-N
CAS Registry Number: 693-89-0
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-1-cyclopentene; 1-Methylcyclopentene; 1-Methyl-1-cyclopentane; Cyc1opentene,l-methyl-; 1-Cyclopentene, 1-methyl; 1-Methylcyclopentene-1
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-4.39	kJ/mol	Chyd	Allinger, Dodziuk, et al., 1982	ALS
Δ_fH°_gas	-3.6 ± 0.75	kJ/mol	Cm	Fuchs and Peacock, 1979	ALS
Δ_fH°_gas	-2.5	kJ/mol	N/A	Good and Smith, 1969	Value computed using Δ_fH_liquid° value of -36.4±0.6 kj/mol from Good and Smith, 1969 and Δ_vapH° value of 33.9 kj/mol from Labbauf and Rossini, 1961.; DRB
Δ_fH°_gas	-4. ± 2.	kJ/mol	Ccb	Labbauf and Rossini, 1961	Heat of formation derived by Cox and Pilcher, 1970; ALS

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	-36.4 ± 0.63	kJ/mol	Ccb	Good and Smith, 1969	ALS
Δ_fH°_liquid	-37.9 ± 0.67	kJ/mol	Ccb	Labbauf and Rossini, 1961	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-3753.8 ± 0.54	kJ/mol	Ccb	Good and Smith, 1969	Corresponding Δ_fHº_liquid = -36.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-3752.4 ± 0.59	kJ/mol	Ccb	Labbauf and Rossini, 1961	Corresponding Δ_fHº_liquid = -37.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
153.1	298.15	Fuchs and Peacock, 1979	DH

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
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
T_boil	349. ± 1.	K	AVG	N/A	Average of 26 out of 28 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	147. ± 2.	K	AVG	N/A	Average of 10 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	32.6 ± 0.3	kJ/mol	C	Fuchs and Peacock, 1979	ALS
Δ_vapH°	32.6 ± 0.2	kJ/mol	GCC	Fuchs and Peacock, 1979	AC
Δ_vapH°	34. ± 2.	kJ/mol	V	Labbauf and Rossini, 1961	Heat of formation derived by Cox and Pilcher, 1970; ALS
Δ_vapH°	33.9	kJ/mol	N/A	Labbauf and Rossini, 1961	DRB

Reduced pressure boiling point

T_boil (K)	Pressure (bar)	Reference	Comment
345.2	1.01	Aldrich Chemical Company Inc., 1990	BS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
33.4	283.	A	Stephenson and Malanowski, 1987	Based on data from 268. to 403. K. See also Dykyj, 1972.; AC

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Reaction thermochemistry data

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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

+ Cyclopentene, 1-methyl- =

By formula: H₂ + C₆H₁₀ = C₆H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-100.8 ± 0.63	kJ/mol	Chyd	Rogers, Crooks, et al., 1987	liquid phase
Δ_rH°	-101.3 ± 0.50	kJ/mol	Chyd	Allinger, Dodziuk, et al., 1982	liquid phase; solvent: Hexane
Δ_rH°	-96.3 ± 0.2	kJ/mol	Chyd	Turner and Garner, 1958	liquid phase; solvent: Acetic acid
Δ_rH°	-96.3 ± 0.2	kJ/mol	Chyd	Turner and Garner, 1957	liquid phase; solvent: Acetic acid
Δ_rH°	-96.3 ± 0.2	kJ/mol	Chyd	Turner and Garner, 1957, 2	liquid phase; solvent: Acetic acid

Cyclopentene, 1-methyl- + =

By formula: C₆H₁₀ + H₂O = C₆H₁₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-55.8 ± 1.4	kJ/mol	Eqk	Taft, Levy, et al., 1952	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -60.0 ± 1.4 kJ/mol; At 308 °K

Cyclopentene, 1-methyl- + =

By formula: C₆H₁₀ + HCl = C₆H₁₁Cl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-54.1 ± 1.6	kJ/mol	Cm	Arnett and Pienta, 1980	liquid phase; solvent: Methylene chloride; Hydrochlorination

Cyclopentene, 1-methyl- =

By formula: C₆H₁₀ = C₆H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	15.8 ± 0.84	kJ/mol	Eqk	Yursha and Kabo, 1975	gas phase

Cyclopentene, 1-methyl- =

By formula: C₆H₁₀ = C₆H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	8.1 ± 0.3	kJ/mol	Eqk	Yursha and Kabo, 1975	gas phase

Cyclopentene, 1-methyl- =

By formula: C₆H₁₀ = C₆H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	7.5 ± 0.2	kJ/mol	Eqk	Yursha and Kabo, 1975	gas phase

References

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

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]

Good and Smith, 1969
Good, W.D.; Smith, N.K., Enthalpies of combustion of toluene, benzene, cyclohexane, cyclohexene, methylcyclopentane, 1-methylcyclopentene, and n-hexane, J. Chem. Eng. Data, 1969, 14, 102-106. [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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K., Enthalpies of hydrogenation of the hexenes, J. Chem. Thermodyn., 1987, 19, 1209-1215. [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]

Taft, Levy, et al., 1952
Taft, R.W., Jr.; Levy, J.B.; Aaron, D.; Hammett, L.P., Rates, equilibrium and temperature coefficients in the reversible hydration of gaseous 1-methylcyclopentene-1 by dilute nitric acid, J. Am. Chem. Soc., 1952, 74, 4735-47. [all data]

Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J., Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions, J. Am. Chem. Soc., 1980, 102, 3329-3334. [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]

Notes

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Symbols used in this document:

C_p,liquid	Constant pressure heat capacity of liquid
T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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