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Cyclopentene

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas8.5kcal/molChydAllinger, Dodziuk, et al., 1982ALS
Deltafgas8.2kcal/molEqkFuruyama, Golden, et al., 1970ALS
Deltafgas7.79kcal/molN/ALabbauf and Rossini, 1961Value computed using «DELTA»fHliquid° value of 4.27±0.63 kj/mol from Labbauf and Rossini, 1961 and «DELTA»vapH° value of 28.37 kj/mol from missing citation.; DRB
Deltafgas7.93kcal/molN/AEpstein, Pitzer, et al., 1949Value computed using «DELTA»fHliquid° value of 4.85±0.67 kj/mol from Epstein, Pitzer, et al., 1949 and «DELTA»vapH° value of 28.37 kj/mol from missing citation.; DRB
Quantity Value Units Method Reference Comment
gas69.230cal/mol*KN/ABeckett C.W., 1948GT

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.58550.Dorofeeva O.V., 1986Although S(298.15 K) value is 1.6 J/mol*K larger than that obtained from calorimetric data [ Beckett C.W., 1948] and calculated in previous works [ Beckett C.W., 1948, Epstein M.B., 1949, Furuyama S., 1970, Draeger J.A., 1983], it is selected here because of using the most reliable vibrational frequencies in [ Dorofeeva O.V., 1986]. The recommended thermodynamic functions are in good agreement with results of detail force-field calculations [ Lenz T.G., 1989, Lenz T.G., 1990]. Discrepancies with above mentioned calculations amount to 1.6-9.1 and 0.8-6.2 J/mol*K for S(T) and Cp(T), respectively.; GT
9.649100.
10.93150.
13.08200.
17.64273.15
19.43 ± 0.48298.15
19.56300.
26.788400.
33.219500.
38.571600.
43.009700.
46.730800.
49.883900.
52.5721000.
54.8761100.
56.8551200.
58.5611300.
60.0361400.
61.3121500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid1.02 ± 0.15kcal/molCcbLabbauf and Rossini, 1961ALS
Deltafliquid1.16 ± 0.16kcal/molCcbEpstein, Pitzer, et al., 1949Unpubished results; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-744.55 ± 0.14kcal/molCcbLabbauf and Rossini, 1961Corresponding «DELTA»fliquid = 1.03 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid48.100cal/mol*KN/AHuffman, Eaton, et al., 1948DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
29.250298.15Huffman, Eaton, et al., 1948T = 12 to 300 K.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, 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:
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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil317. ± 2.KAVGN/AAverage of 28 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus138. ± 1.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple138.13KN/AHuffman, Eaton, et al., 1948, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC
Quantity Value Units Method Reference Comment
Tc506.5 ± 0.5KN/ATsonopoulos and Ambrose, 1996 
Tc507.6KN/ATeja and Anselme, 1990Uncertainty assigned by TRC = 0.4 K; TRC
Tc507.0KN/ATeja and Rosenthal, 1990Uncertainty assigned by TRC = 0.6 K; TRC
Tc506.1KN/AAmbrose and Grant, 1957Uncertainty assigned by TRC = 0.15 K; TRC
Quantity Value Units Method Reference Comment
Pc47.4 ± 0.5atmN/ATsonopoulos and Ambrose, 1996 
Pc47.39atmN/ATeja and Rosenthal, 1990Uncertainty assigned by TRC = 0.30 atm; TRC
Quantity Value Units Method Reference Comment
Vc0.245l/molN/ATsonopoulos and Ambrose, 1996 
Quantity Value Units Method Reference Comment
rhoc4.08 ± 0.05mol/lN/ATsonopoulos and Ambrose, 1996 
rhoc4.08mol/lN/ATeja and Anselme, 1990Uncertainty assigned by TRC = 0.09 mol/l; TRC
Quantity Value Units Method Reference Comment
Deltavap6.780kcal/molVLister, 1941Halogenation at 27 C; ALS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
7.15264.AStephenson and Malanowski, 1987Based on data from 249. - 318. K.; AC
5.93299.MMForziati, Camin, et al., 1950Based on data from 289. - 318. K.; AC
6.79300.N/ALister, 1941Based on data from 230. - 293. K.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
0.803138.1Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
1.3287.07Domalski and Hearing, 1996CAL
5.813138.1

Enthalpy of phase transition

DeltaHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.114687.07crystaline, IIcrystaline, IHuffman, Eaton, et al., 1948DH
0.80387138.13crystaline, IliquidHuffman, Eaton, et al., 1948DH

Entropy of phase transition

DeltaStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
2.2787.07crystaline, IIcrystaline, IHuffman, Eaton, et al., 1948DH
5.820138.13crystaline, IliquidHuffman, Eaton, et al., 1948DH

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, 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 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 = Cyclopentane

By formula: H2 + C5H8 = C5H10

Quantity Value Units Method Reference Comment
Deltar-26.94 ± 0.13kcal/molChydAllinger, Dodziuk, et al., 1982liquid phase; solvent: Hexane
Deltar-26.8 ± 0.2kcal/molChydRoth and Lennartz, 1980liquid phase; solvent: Cyclohexane
Deltar-26.04 ± 0.44kcal/molChydTurner, Jarrett, et al., 1973liquid phase; solvent: Acetic acid
Deltar-26.2 ± 0.2kcal/molChydRogers and McLafferty, 1971liquid phase; solvent: Hydrocarbon
Deltar-26.67 ± 0.06kcal/molChydDolliver, Gresham, et al., 1937gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -26.92 ± 0.06 kcal/mol; At 355 °K

Cyclopentene + Trifluoroacetic acid = Trifluoroacetic acid, cyclopentyl ester

By formula: C5H8 + C2HF3O2 = C7H9F3O2

Quantity Value Units Method Reference Comment
Deltar-9.167 ± 0.044kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis

Cyclopentene + Bromine = Cyclopentane, 1,2-dibromo,trans-

By formula: C5H8 + Br2 = C5H8Br2

Quantity Value Units Method Reference Comment
Deltar-28.61 ± 0.60kcal/molCmLister, 1941gas phase; Halogenation at 27 C

Cyclopentane + Iodine = 2Hydrogen iodide + Cyclopentene

By formula: C5H10 + I2 = 2HI + C5H8

Quantity Value Units Method Reference Comment
Deltar24.40kcal/molEqkFuruyama, Golden, et al., 1970gas phase

2Hydrogen iodide + 1,3-Cyclopentadiene = Cyclopentene + Iodine

By formula: 2HI + C5H6 = C5H8 + I2

Quantity Value Units Method Reference Comment
Deltar-21.4kcal/molEqkFuruyama, Golden, et al., 1970gas phase

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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-3720
NIST MS number 227659

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

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

Furuyama, Golden, et al., 1970
Furuyama, S.; Golden, D.M.; Benson, S.W., Thermochemistry of cyclopentene and cyclopentadiene from studies of gas-phase equilibria, J. Chem. Thermodyn., 1970, 2, 161-169. [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]

Epstein, Pitzer, et al., 1949
Epstein, M.B.; Pitzer, K.S.; Rossini, F.D., Heats, equilibrium constants, and free energies of formation of cyclopentene and cyclohexene, J. Res. NBS, 1949, 42, 379-382. [all data]

Beckett C.W., 1948
Beckett C.W., The thermodynamic properties and molecular structure of cyclopentene and cyclohexene, J. Am. Chem. Soc., 1948, 70, 4227-4230. [all data]

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Epstein M.B., 1949
Epstein M.B., Heats, equilibrium constants, and free energies of formation of cyclopentene and cyclohexene, J. Res. Nat. Bur. Stand., 1949, 42, 379-382. [all data]

Furuyama S., 1970
Furuyama S., Thermochemistry of cyclopentene and cyclopentadiene from studies of gas-phase equilibria, J. Chem. Thermodyn., 1970, 2, 161-169. [all data]

Draeger J.A., 1983
Draeger J.A., Chemical thermodynamic properties of molecules that undergo inversion. I. Aniline, methylamine, cyclopropylamine, and cyclopentene, J. Chem. Thermodyn., 1983, 15, 367-376. [all data]

Lenz T.G., 1989
Lenz T.G., Force-field calculations giving accurate conformation, Hf(T), S(T), and Cp(T) for unsaturated acyclic and cyclic hydrocarbons, J. Phys. Chem., 1989, 93, 1588-1592. [all data]

Lenz T.G., 1990
Lenz T.G., Force field calculation of equilibrium thermodynamic properties: Diels-Alder reaction of 1,3-butadiene and ethylene and Diels-Alder dimerization of 1,3-butadiene, J. Comput. Chem., 1990, 11, 351-360. [all data]

Huffman, Eaton, et al., 1948
Huffman, H.M.; Eaton, M.; Oliver, G.D., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentene and cyclohexene, J. Am. Chem. Soc., 1948, 70, 2911-2914. [all data]

Huffman, Eaton, et al., 1948, 2
Huffman, H.M.; Eaton, M.; Oliver, G.D., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentene and cyclohexene, J. Am. Chem. Soc., 1948, 70, 2911. [all data]

Tsonopoulos and Ambrose, 1996
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons, J. Chem. Eng. Data, 1996, 41, 645-656. [all data]

Teja and Anselme, 1990
Teja, A.S.; Anselme, M.J., The critical properties of thermally stable and unstable fluids. II. 1986 results, AIChE Symp. Ser., 1990, 86, 279, 122-7. [all data]

Teja and Rosenthal, 1990
Teja, A.S.; Rosenthal, D.J., The Critical Pressures and Temperatures of Twelve Substances Using A Low Residence Time Flow Apparatus, AIChE Symp. Ser., 1990, 86, 279, 133-7. [all data]

Ambrose and Grant, 1957
Ambrose, D.; Grant, D.G., The Critical Temperatures of Some Hydrocarbons and Pyridine Bases, Trans. Faraday Soc., 1957, 53, 771. [all data]

Lister, 1941
Lister, M.W., Heats of organic reactions. X. Heats of bromination of cyclic olefins, J. Am. Chem. Soc., 1941, 63, 143-149. [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]

Forziati, Camin, et al., 1950
Forziati, A.F.; Camin, D.L.; Rossini, F.D., Density, refractive index, boiling point, and vapor pressure of eight monoolefin (1-alkene), six pentadiene, and two cyclomonoolefin hydrocarbons, J. RES. NATL. BUR. STAN., 1950, 45, 5, 406, https://doi.org/10.6028/jres.045.044 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Roth and Lennartz, 1980
Roth, W.R.; Lennartz, H.W., Heats of hydrogenation. I. Determination of heats of hydrogenation with an isothermal titration calorimeter, Chem. Ber., 1980, 113, 1806-1817. [all data]

Turner, Jarrett, et al., 1973
Turner, R.B.; Jarrett, A.D.; Goebel, P.; Mallon, B.J., Heats of hydrogenation. 9. Cyclic acetylenes and some miscellaneous olefins, J. Am. Chem. Soc., 1973, 95, 790-792. [all data]

Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J., A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring, Tetrahedron, 1971, 27, 3765-3775. [all data]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [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]

Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A., Enthalpies of hydration of alkenes. 3. Cycloalkenes, J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]


Notes

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