Cyclopentene, 1-methyl-
- Formula: C6H10
- Molecular weight: 82.1436
- 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, 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
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -1.05 | kcal/mol | Chyd | Allinger, Dodziuk, et al., 1982 | ALS |
ΔfH°gas | -0.86 ± 0.18 | kcal/mol | Cm | Fuchs and Peacock, 1979 | ALS |
ΔfH°gas | -0.60 | kcal/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 | -0.9 ± 0.5 | kcal/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 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 | -8.71 ± 0.15 | kcal/mol | Ccb | Good and Smith, 1969 | ALS |
ΔfH°liquid | -9.05 ± 0.16 | kcal/mol | Ccb | Labbauf and Rossini, 1961 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -897.17 ± 0.13 | kcal/mol | Ccb | Good and Smith, 1969 | Corresponding ΔfHºliquid = -8.71 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -896.85 ± 0.14 | kcal/mol | Ccb | Labbauf and Rossini, 1961 | Corresponding ΔfHºliquid = -9.03 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
36.59 | 298.15 | Fuchs and Peacock, 1979 | DH |
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:
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 |
---|---|---|---|---|---|
Tboil | 349. ± 1. | K | AVG | N/A | Average of 26 out of 28 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 147. ± 2. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.80 ± 0.06 | kcal/mol | C | Fuchs and Peacock, 1979 | ALS |
ΔvapH° | 7.79 ± 0.05 | kcal/mol | GCC | Fuchs and Peacock, 1979 | AC |
ΔvapH° | 8.1 ± 0.4 | kcal/mol | V | Labbauf and Rossini, 1961 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
ΔvapH° | 8.10 | kcal/mol | N/A | Labbauf and Rossini, 1961 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
345.2 | 0.992 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.98 | 283. | A | Stephenson and Malanowski, 1987 | Based on data from 268. 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: H2 + C6H10 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -24.09 ± 0.15 | kcal/mol | Chyd | Rogers, Crooks, et al., 1987 | liquid phase |
ΔrH° | -24.22 ± 0.12 | kcal/mol | Chyd | Allinger, Dodziuk, et al., 1982 | liquid phase; solvent: Hexane |
ΔrH° | -23.01 ± 0.04 | kcal/mol | Chyd | Turner and Garner, 1958 | liquid phase; solvent: Acetic acid |
ΔrH° | -23.01 ± 0.04 | kcal/mol | Chyd | Turner and Garner, 1957 | liquid phase; solvent: Acetic acid |
ΔrH° | -23.01 ± 0.04 | kcal/mol | Chyd | Turner and Garner, 1957, 2 | liquid phase; solvent: Acetic acid |
By formula: C6H10 + H2O = C6H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -13.34 ± 0.34 | kcal/mol | Eqk | Taft, Levy, et al., 1952 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -14.34 ± 0.34 kcal/mol; At 308 °K |
By formula: C6H10 + HCl = C6H11Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -12.92 ± 0.38 | kcal/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
By formula: C6H10 = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 3.78 ± 0.20 | kcal/mol | Eqk | Yursha and Kabo, 1975 | gas phase |
By formula: C6H10 = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1.93 ± 0.07 | kcal/mol | Eqk | Yursha and Kabo, 1975 | gas phase |
By formula: C6H10 = C6H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1.79 ± 0.04 | kcal/mol | Eqk | Yursha and Kabo, 1975 | gas phase |
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 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) | 195.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 188.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.59 | EI | Lossing and Traeger, 1975 | LLK |
8.60 ± 0.01 | PE | Rang, Paldoia, et al., 1974 | LLK |
9.12 ± 0.05 | EI | Praet, 1970 | RDSH |
8.55 ± 0.01 | PI | Praet, 1970 | RDSH |
8.54 ± 0.01 | PE | Praet and Delwiche, 1970 | RDSH |
8.62 ± 0.02 | EI | Winters and Collins, 1969 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 13.23 ± 0.21 | ? | EI | Winters and Collins, 1969 | RDSH |
C3H5+ | 13.7 | C4H7 | EI | Shikhmamedbekova, Aslanov, et al., 1970 | RDSH |
C3H5+ | 14.9 ± 0.1 | ? | EI | Praet, 1970 | RDSH |
C3H5+ | 12.45 ± 0.13 | ? | EI | Winters and Collins, 1969 | RDSH |
C4H5+ | 13.14 ± 0.09 | ? | EI | Winters and Collins, 1969 | RDSH |
C4H6+ | 12.33 ± 0.05 | C2H4 | EI | Praet, 1970 | RDSH |
C4H6+ | 11.02 ± 0.12 | ? | EI | Winters and Collins, 1969 | RDSH |
C5H5+ | 13.45 ± 0.19 | ? | EI | Winters and Collins, 1969 | RDSH |
C5H7+ | 8.59 | CH3 | EI | Lossing and Traeger, 1975, 2 | LLK |
C5H7+ | 10.19 | H | EI | Lossing and Traeger, 1975 | LLK |
C5H7+ | 11.59 ± 0.05 | CH3 | EI | Praet, 1970 | RDSH |
C5H7+ | 9.99 ± 0.09 | CH3 | EI | Winters and Collins, 1969 | RDSH |
C6H7+ | 12.40 ± 0.17 | H2+H | EI | Winters and Collins, 1969 | RDSH |
C6H9+ | 11.97 ± 0.05 | H | EI | Praet, 1970 | RDSH |
C6H9+ | 10.59 ± 0.13 | H | EI | Winters and Collins, 1969 | RDSH |
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 | Japan AIST/NIMC Database- Spectrum MS-NW-3064 |
NIST MS number | 231297 |
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]
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]
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]
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]
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]
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]
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]
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]
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
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid 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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