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
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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 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 |
|---|---|---|---|---|---|
| ΔfH°gas | -4.39 | kJ/mol | Chyd | Allinger, Dodziuk, et al., 1982 | ALS |
| ΔfH°gas | -3.6 ± 0.75 | kJ/mol | Cm | Fuchs and Peacock, 1979 | ALS |
| ΔfH°gas | -2.5 | kJ/mol | N/A | Good and Smith, 1969 | Value computed using ΔfHliquid° value of -36.4±0.6 kj/mol from Good and Smith, 1969 and ΔvapH° value of 33.9 kj/mol from Labbauf and Rossini, 1961.; DRB |
| ΔfH°gas | -4. ± 2. | kJ/mol | Ccb | Labbauf and Rossini, 1961 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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 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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -36.4 ± 0.63 | kJ/mol | Ccb | Good and Smith, 1969 | ALS |
| ΔfH°liquid | -37.9 ± 0.67 | kJ/mol | Ccb | Labbauf and Rossini, 1961 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3753.8 ± 0.54 | kJ/mol | Ccb | Good and Smith, 1969 | Corresponding ΔfHºliquid = -36.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -3752.4 ± 0.59 | kJ/mol | Ccb | Labbauf and Rossini, 1961 | Corresponding ΔfHºliquid = -37.8 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 |
|---|---|---|---|
| 153.1 | 298.15 | Fuchs and Peacock, 1979 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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: 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -100.8 ± 0.63 | kJ/mol | Chyd | Rogers, Crooks, et al., 1987 | liquid phase |
| ΔrH° | -101.3 ± 0.50 | kJ/mol | Chyd | Allinger, Dodziuk, et al., 1982 | liquid phase; solvent: Hexane |
| ΔrH° | -96.3 ± 0.2 | kJ/mol | Chyd | Turner and Garner, 1958 | liquid phase; solvent: Acetic acid |
| ΔrH° | -96.3 ± 0.2 | kJ/mol | Chyd | Turner and Garner, 1957 | liquid phase; solvent: Acetic acid |
| ΔrH° | -96.3 ± 0.2 | kJ/mol | Chyd | Turner and Garner, 1957, 2 | liquid phase; solvent: Acetic acid |
+
=
By formula: C6H10 + H2O = C6H12O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -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 |
+
=
By formula: C6H10 + HCl = C6H11Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -54.1 ± 1.6 | kJ/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
=
By formula: C6H10 = C6H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.8 ± 0.84 | kJ/mol | Eqk | Yursha and Kabo, 1975 | gas phase |
=
By formula: C6H10 = C6H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 8.1 ± 0.3 | kJ/mol | Eqk | Yursha and Kabo, 1975 | gas phase |
=
By formula: C6H10 = C6H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 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, Reaction thermochemistry data, 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]
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]
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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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