Cyclopentene, 1-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 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
Δfgas-4.39kJ/molChydAllinger, Dodziuk, et al., 1982ALS
Δfgas-3.6 ± 0.75kJ/molCmFuchs and Peacock, 1979ALS
Δfgas-2.5kJ/molN/AGood and Smith, 1969Value 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
Δfgas-4. ± 2.kJ/molCcbLabbauf and Rossini, 1961Heat 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
Δfliquid-36.4 ± 0.63kJ/molCcbGood and Smith, 1969ALS
Δfliquid-37.9 ± 0.67kJ/molCcbLabbauf and Rossini, 1961ALS
Quantity Value Units Method Reference Comment
Δcliquid-3753.8 ± 0.54kJ/molCcbGood and Smith, 1969Corresponding Δfliquid = -36.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3752.4 ± 0.59kJ/molCcbLabbauf and Rossini, 1961Corresponding Δfliquid = -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
153.1298.15Fuchs 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:
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
Tboil349. ± 1.KAVGN/AAverage of 26 out of 28 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus147. ± 2.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Δvap32.6 ± 0.3kJ/molCFuchs and Peacock, 1979ALS
Δvap32.6 ± 0.2kJ/molGCCFuchs and Peacock, 1979AC
Δvap34. ± 2.kJ/molVLabbauf and Rossini, 1961Heat of formation derived by Cox and Pilcher, 1970; ALS
Δvap33.9kJ/molN/ALabbauf and Rossini, 1961DRB

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
345.21.01Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
33.4283.AStephenson and Malanowski, 1987Based on data from 268. to 403. 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:


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

Hydrogen + Cyclopentene, 1-methyl- = Cyclopentane, methyl-

By formula: H2 + C6H10 = C6H12

Quantity Value Units Method Reference Comment
Δr-100.8 ± 0.63kJ/molChydRogers, Crooks, et al., 1987liquid phase
Δr-101.3 ± 0.50kJ/molChydAllinger, Dodziuk, et al., 1982liquid phase; solvent: Hexane
Δr-96.3 ± 0.2kJ/molChydTurner and Garner, 1958liquid phase; solvent: Acetic acid
Δr-96.3 ± 0.2kJ/molChydTurner and Garner, 1957liquid phase; solvent: Acetic acid
Δr-96.3 ± 0.2kJ/molChydTurner and Garner, 1957, 2liquid phase; solvent: Acetic acid

Cyclopentene, 1-methyl- + Water = Cyclopentanol, 2-methyl-, cis-

By formula: C6H10 + H2O = C6H12O

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

Cyclopentene, 1-methyl- + Hydrogen chloride = 1-Chloro-1-methylcyclopentane

By formula: C6H10 + HCl = C6H11Cl

Quantity Value Units Method Reference Comment
Δr-54.1 ± 1.6kJ/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochlorination

Cyclopentene, 1-methyl- = Cyclopentane, methylene-

By formula: C6H10 = C6H10

Quantity Value Units Method Reference Comment
Δr15.8 ± 0.84kJ/molEqkYursha and Kabo, 1975gas phase

Cyclopentene, 1-methyl- = Cyclopentene, 3-methyl-

By formula: C6H10 = C6H10

Quantity Value Units Method Reference Comment
Δr8.1 ± 0.3kJ/molEqkYursha and Kabo, 1975gas phase

Cyclopentene, 1-methyl- = Cyclopentene, 4-methyl-

By formula: C6H10 = C6H10

Quantity Value Units Method Reference Comment
Δr7.5 ± 0.2kJ/molEqkYursha and Kabo, 1975gas 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)816.5kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity787.1kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.59EILossing and Traeger, 1975LLK
8.60 ± 0.01PERang, Paldoia, et al., 1974LLK
9.12 ± 0.05EIPraet, 1970RDSH
8.55 ± 0.01PIPraet, 1970RDSH
8.54 ± 0.01PEPraet and Delwiche, 1970RDSH
8.62 ± 0.02EIWinters and Collins, 1969RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.23 ± 0.21?EIWinters and Collins, 1969RDSH
C3H5+13.7C4H7EIShikhmamedbekova, Aslanov, et al., 1970RDSH
C3H5+14.9 ± 0.1?EIPraet, 1970RDSH
C3H5+12.45 ± 0.13?EIWinters and Collins, 1969RDSH
C4H5+13.14 ± 0.09?EIWinters and Collins, 1969RDSH
C4H6+12.33 ± 0.05C2H4EIPraet, 1970RDSH
C4H6+11.02 ± 0.12?EIWinters and Collins, 1969RDSH
C5H5+13.45 ± 0.19?EIWinters and Collins, 1969RDSH
C5H7+8.59CH3EILossing and Traeger, 1975, 2LLK
C5H7+10.19HEILossing and Traeger, 1975LLK
C5H7+11.59 ± 0.05CH3EIPraet, 1970RDSH
C5H7+9.99 ± 0.09CH3EIWinters and Collins, 1969RDSH
C6H7+12.40 ± 0.17H2+HEIWinters and Collins, 1969RDSH
C6H9+11.97 ± 0.05HEIPraet, 1970RDSH
C6H9+10.59 ± 0.13HEIWinters and Collins, 1969RDSH

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


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

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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, IR Spectrum, Mass spectrum (electron ionization), References