1,3-Cyclopentadiene

Formula: C₅H₆
Molecular weight: 66.1011
IUPAC Standard InChI: InChI=1S/C5H6/c1-2-4-5-3-1/h1-4H,5H2
IUPAC Standard InChIKey: ZSWFCLXCOIISFI-UHFFFAOYSA-N
CAS Registry Number: 542-92-7
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: Cyclopentadiene; Pentole; Pyropentylene; R-Pentine
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	33.2	kcal/mol	Chyd	Roth, Adamczak, et al., 1991	ALS
Δ_fH°_gas	31.89	kcal/mol	Eqk	Furuyama, Golden, et al., 1970	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-707. ± 7.	kcal/mol	Ccb	Wassermann, 1935	Corresponding Δ_fHº_gas = 32. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	65.600	cal/mol*K	N/A	Furuyama S., 1970	This a second law entropy value was obtained from study of gas-phase equilibrium. The value of S(298.2 K)=270.3(4.2) J/mol*K was obtained from other equilibrium study [ Grant C.J., 1969].; GT

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
7.957	50.	Dorofeeva O.V., 1986	Recommended S(T) values differ from other statistically calculated values [ Turnbull A.G., 1967, Furuyama S., 1970] up to 2.6 J/molK. Discrepancies in Cp(T) values amount to 1.3-4.3 J/molK. There is an excellent agreement between selected values of S(T) and Cp(T) and those obtained by ab initio calculation [ Karni M., 1991].; GT
8.375	100.
9.637	150.
11.84	200.
16.32	273.15
18.01 ± 0.48	298.15
18.14	300.
24.689	400.
30.222	500.
34.663	600.
38.250	700.
41.207	800.
43.683	900.
45.782	1000.
47.572	1100.
49.109	1200.
50.430	1300.
51.570	1400.
52.562	1500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compiled by: Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
S°_liquid	43.67	cal/mol*K	N/A	Lebedev and Lityagov, 1977

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
27.56	298.15	Lebedev and Lityagov, 1977	T = 14 to 330 K.

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

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

Additional Data

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Owner	COBLENTZ SOCIETY Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.
Origin	WYANDOTTE CHEMICALS CORP., WYANDOTTE, MICHIGAN, USA
Source reference	COBLENTZ NO. 2691
Date	Not specified, most likely prior to 1970
Name(s)	1,3-cyclopentadiene
State	LIQUID
Instrument	Not specified, most likely a prism, grating, or hybrid spectrometer.
Path length	0.003 CM
Resolution	4
Sampling procedure	TRANSMISSION
Data processing	DIGITIZED BY NIST FROM HARD COPY
Boiling point	41 C

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

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Due to licensing restrictions, this spectrum cannot be downloaded.

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.
NIST MS number	196

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Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	OV-101	100.	545.	Diez, Guillen, et al., 1990	N2; Column length: 25. m; Column diameter: 0.23 mm
Capillary	OV-101	80.	542.	Diez, Guillen, et al., 1990	N2; Column length: 25. m; Column diameter: 0.23 mm
Capillary	Squalane	100.	534.7	Diez, Guillen, et al., 1990	N2; Column length: 45. m; Column diameter: 0.5 mm
Capillary	Squalane	80.	510.5	Diez, Guillen, et al., 1990	N2; Column length: 45. m; Column diameter: 0.5 mm
Capillary	SE-54	100.	552.5	Diez, Guillen, et al., 1990	N2; Column length: 25. m; Column diameter: 0.22 mm
Capillary	SE-54	80.	549.5	Diez, Guillen, et al., 1990	N2; Column length: 25. m; Column diameter: 0.22 mm
Packed	Squalane	70.	527.	Safina, Poznyak, et al., 1989	He, Risorb (0.2-0.3 mm); Column length: 2. m
Capillary	Squalane	50.	521.7	Papazova, Milina, et al., 1988	Column length: 50. m; Column diameter: 0.25 mm
Capillary	BP-1	100.	543.	Bermejo, Blanco, et al., 1987	N2; Column length: 12. m; Column diameter: 0.22 mm
Capillary	BP-1	80.	541.	Bermejo, Blanco, et al., 1987	N2; Column length: 12. m; Column diameter: 0.22 mm
Capillary	OV-101	100.	545.	Bermejo, Blanco, et al., 1987	N2; Column length: 25. m; Column diameter: 0.23 mm
Capillary	OV-101	80.	542.	Bermejo, Blanco, et al., 1987	N2; Column length: 25. m; Column diameter: 0.23 mm
Capillary	Squalane	64.	523.	Sojak, Ruman, et al., 1987	50. m/0.25 mm/0.25 μm, H2
Capillary	SE-30	130.	546.	Bredael, 1982	Column length: 100. m; Column diameter: 0.5 mm
Capillary	SE-30	80.	540.	Bredael, 1982	Column length: 100. m; Column diameter: 0.5 mm
Capillary	Squalane	50.	521.8	Bajus, Veselý, et al., 1979	Column length: 100. m; Column diameter: 0.25 mm
Capillary	Squalane	50.	521.6	Bajus, Veselý, et al., 1979, 2	Column length: 100. m; Column diameter: 0.25 mm
Packed	Squalane	27.	518.	Bogoslovsky, Anvaer, et al., 1978
Packed	Squalane	49.	521.	Bogoslovsky, Anvaer, et al., 1978
Packed	Squalane	67.	527.	Bogoslovsky, Anvaer, et al., 1978
Packed	Squalane	86.	530.	Bogoslovsky, Anvaer, et al., 1978
Capillary	Squalane	40.	520.6	Stopp, Engewald, et al., 1978	Column length: 70. m; Column diameter: 0.23 mm
Capillary	Squalane	27.	516.61	Schomburg and Dielmann, 1973	Column length: 100. m; Column diameter: 0.25 mm
Packed	Squalane	27.	519.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	49.	522.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	67.	528.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
Packed	Squalane	86.	530.	Hively and Hinton, 1968	He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm

Kovats' RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Petrocol DH-100	538.1	Haagen-Smit Laboratory, 1997	He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min)
Capillary	DB-1	533.	Hoekman, 1993	60. m/0.32 mm/1.0 μm, He; Program: -40 C for 12 min; -40 - 125 C at 3 deg.min; 125-185 C at 6 deg/min; 185 - 220 C at 20 deg/min; hold 220 C for 2 min

Kovats' RI, polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	Carbowax 20M	64.	745.7	Sojak, Ruman, et al., 1987	50. m/0.25 mm/0.25 μm, H2

Kovats' RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	735.	Umano and Shibamoto, 1987	He, 40. C @ 10. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 200. C

Normal alkane RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	Methyl Silicone	50.	522.	N/A	N2; Column length: 74.6 m; Column diameter: 0.28 mm

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Polydimethyl siloxane: CP-Sil 5 CB	528.	Bramston-Cook, 2013	60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min
Capillary	PONA	525.	Zhang, Ding, et al., 2009	50. m/0.20 mm/0.50 μm, Nitrogen, 35. C @ 15. min, 2. K/min, 200. C @ 10. min

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Squalane	523.	Chen, 2008	Program: not specified
Capillary	PONA	538.	Perkin Elmer Instruments, 2002	Column length: 100. m; Phase thickness: 0.50 μm; Program: not specified
Capillary	OV-101	530.	Zenkevich, 1998	He; Column length: 25. m; Column diameter: 0.20 mm; Program: not specified
Capillary	OV-101	535.	Zenkevich, 1998	He; Column length: 25. m; Column diameter: 0.20 mm; Program: not specified
Capillary	OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.	540.	Waggott and Davies, 1984	Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

Lee's RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5	97.2	Shao, Wang, et al., 2006	30. m/0.3 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min, 200. C @ 15. min

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521. [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]

Wassermann, 1935
Wassermann, A., The mechanism of additions to double bonds. Part I. Thermochemistry and kinetics of a diene synthesis, J. Chem. Soc., 1935, 828-838. [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]

Grant C.J., 1969
Grant C.J., Reversibility in the gas-phase decomposition of cyclopentene. The entropy of cyclopentadiene, J. Chem. Soc. Chem. Comm., 1969, 667-668. [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]

Turnbull A.G., 1967
Turnbull A.G., Thermochemistry of biscyclopentadienyl metal compounds, Austral. J. Chem., 1967, 20, 2059-2067. [all data]

Karni M., 1991
Karni M., Ab initio calculations and ideal gas thermodynamic functions of cyclopentadiene and cyclopentadiene derivatives, J. Phys. Chem. Ref. Data, 1991, 20, 665-683. [all data]

Lebedev and Lityagov, 1977
Lebedev, B.V.; Lityagov, V.Ya., Thermodynamics of polypentenamer synthesis reactions, Vysokomol. Soedin., 1977, B19, 558-560. [all data]

Diez, Guillen, et al., 1990
Diez, M.A.; Guillen, M.D.; Blanco, C.G.; Bermejo, J., Chromatographic study of methylcyclopentadiene dimers and iso-dimers and determination of their boiling points, J. Chromatogr., 1990, 508, 363-374, https://doi.org/10.1016/S0021-9673(00)91279-2 . [all data]

Safina, Poznyak, et al., 1989
Safina, L.R.; Poznyak, T.I.; Lisitsyn, D.M.; Kiseleva, E.V.; Kovalev, G.I., Selective gas-chromatographic determination of trace unsaturated and aromatic-hydrocarbons in complex-mixtures, J. Appl. Chem. USSR (Engl. Transl.), 1989, 44, 5, 749-754. [all data]

Papazova, Milina, et al., 1988
Papazova, D.; Milina, R.; Dimov, N., Comparative evaluation of retention of hydrocarbons present in the C₅-petroleum fraction of methylsilicone and squalane phases, Chromatographia, 1988, 25, 3, 177-180, https://doi.org/10.1007/BF02316441 . [all data]

Bermejo, Blanco, et al., 1987
Bermejo, J.; Blanco, C.G.; Diez, M.A.; Guillén, M.D., Kováts retention indices of selected mono and polycyclic olefins, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1987, 10, 8, 461-463, https://doi.org/10.1002/jhrc.1240100809 . [all data]

Sojak, Ruman, et al., 1987
Sojak, L.; Ruman, J.; Janak, J., Characterization of Monoalkylcyclopentadiens by Retention-Structure Correlation in Capillary Gas Chromatography, J. Chromatogr., 1987, 391, 79-87, https://doi.org/10.1016/S0021-9673(01)94306-7 . [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

Bajus, Veselý, et al., 1979
Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A., Steam cracking of hydrocarbons. 2. Pyrolysis of methylcyclohexane, Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 2, 135-142, https://doi.org/10.1021/i360070a012 . [all data]

Bajus, Veselý, et al., 1979, 2
Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A., Steam cracking of hydrocarbons. 1. Pyrolysis of heptane, Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 1, 30-37, https://doi.org/10.1021/i360069a007 . [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Stopp, Engewald, et al., 1978
Stopp, I.; Engewald, W.; Kühn, H.; Welsch, Th., Molekülstruktur und retentionsverhalten. VIII. Zum gaschromatographischen retentionsverhalten von dicyclopentadienderivaten, J. Chromatogr., 1978, 147, 21-30, https://doi.org/10.1016/S0021-9673(00)85113-4 . [all data]

Schomburg and Dielmann, 1973
Schomburg, G.; Dielmann, G., Identification by means of retention parameters, J. Chromatogr. Sci., 1973, 11, 3, 151-159, https://doi.org/10.1093/chromsci/11.3.151 . [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory, Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]

Hoekman, 1993
Hoekman, S.K., Improved gas chromatography procedure for speciated hydrocarbon measurements of vehicle emissions, J. Chromatogr., 1993, 639, 2, 239-253, https://doi.org/10.1016/0021-9673(93)80260-F . [all data]

Umano and Shibamoto, 1987
Umano, K.; Shibamoto, T., Analysis of headspace volatiles from overheated beef fat, J. Agric. Food Chem., 1987, 35, 1, 14-18, https://doi.org/10.1021/jf00073a004 . [all data]

Bramston-Cook, 2013
Bramston-Cook, R., Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]

Zhang, Ding, et al., 2009
Zhang, X.; Ding, L.; Sun, Z.; Song, L.; Sun, T., Study on quantitative structure-retention relationships for hydrocarbons in FCC gasoline, Chromatographia, 2009, 70, 3/4, 511-518, https://doi.org/10.1365/s10337-009-1174-0 . [all data]

Chen, 2008
Chen, H.-F., Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression, Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003 . [all data]

Perkin Elmer Instruments, 2002
Perkin Elmer Instruments, Detailed hydrocarbon analysis (DHAX) Model 4015, 2002, retrieved from http://www.perkinelmer.com/instruments. [all data]

Zenkevich, 1998
Zenkevich, I.G., Application of Methods of Molecular Dynamics in Chromato-Spectral Identification of ISomeric Products of Organic reactions (in Russian), Zh. Org. Khim., 1998, 34, 10, 1463-1470. [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Shao, Wang, et al., 2006
Shao, X.; Wang, G.; Sun, Y.; Zhang, R.; Xie, K.; Liu, H., Determination and Characterization of the Pyrolysis Products of Isoprocarb by GC-MS, J. Chromatogr. Sci., 2006, 44, 3, 141-147, https://doi.org/10.1093/chromsci/44.3.141 . [all data]

Notes

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

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
S°_gas	Entropy of gas at standard conditions
S°_liquid	Entropy of liquid at standard conditions
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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NIST Chemistry WebBook, SRD 69

1,3-Cyclopentadiene

Data at NIST subscription sites:

Gas phase thermochemistry data

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

Constant pressure heat capacity of liquid

IR Spectrum

Condensed Phase Spectrum

Help

Credits

Additional Data

Mass spectrum (electron ionization)

Spectrum

Help

Credits

Additional Data

Gas Chromatography

Kovats' RI, non-polar column, isothermal

Kovats' RI, non-polar column, custom temperature program

Kovats' RI, polar column, isothermal

Kovats' RI, polar column, temperature ramp

Normal alkane RI, non-polar column, isothermal

Normal alkane RI, non-polar column, temperature ramp

Normal alkane RI, non-polar column, custom temperature program

Lee's RI, non-polar column, temperature ramp

References

Notes