Cyclopentane - The NIST WebBook

Cyclopentane

• Formula: C5H10
• Molecular weight: 70.1329
• IUPAC Standard InChI: InChI=1S/C5H10/c1-2-4-5-3-1/h1-5H2 Copy
• IUPAC Standard InChIKey: RGSFGYAAUTVSQA-UHFFFAOYSA-N Copy
• CAS Registry Number: 287-92-3
• Chemical structure: This structure is also available as a 2d Mol file or as a computed 3d SD file View 3d structure (requires JavaScript / HTML 5)
• Other names: Pentamethylene; UN 1146
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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	-105.6 ± 1.8	kJ/mol	Ccb	Spitzer and Huffman, 1947	ALS
ΔfH°liquid	-105.9 ± 0.75	kJ/mol	Ccb	Prosen, Johnson, et al., 1946	ALS
Quantity	Value	Units	Method	Reference	Comment
ΔcH°liquid	-3291.4 ± 0.6	kJ/mol	Ccb	Kaarsemaker and Coops, 1952	Corresponding ΔfHºliquid = -105.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
ΔcH°liquid	-3291.2 ± 1.3	kJ/mol	Ccb	Spitzer and Huffman, 1947	Corresponding ΔfHºliquid = -105.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
ΔcH°liquid	-3290.9 ± 0.71	kJ/mol	Ccb	Prosen, Johnson, et al., 1946	Corresponding ΔfHºliquid = -105.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°liquid	204.14	J/mol*K	N/A	Douslin and Huffman, 1946	DH
S°liquid	204.47	J/mol*K	N/A	Aston, Fink, et al., 1943	DH
S°liquid	206.7	J/mol*K	N/A	Jacobs and Parks, 1934	Extrapolation below 90 K, 53.09 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K)	Temperature (K)	Reference	Comment
126.74	298.15	Tanaka, 1985	DH
126.17	293.15	Siddiqi, Svejda, et al., 1983	DH
126.873	298.15	Fortier, D'Arcy, et al., 1979	DH
127.28	298.15	Jolicoeur, Boileau, et al., 1975	DH
127.44	300.	Szasz, Morrison, et al., 1947	T = 14 to 300 K.; DH
126.78	298.15	Douslin and Huffman, 1946	T = 12 to 300 K.; DH
128.83	298.15	Aston, Fink, et al., 1943	T = 15 to 300 K.; DH
125.90	293.7	Jacobs and Parks, 1934	T = 93 to 294 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

Go To: Top, 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 as indicated in comments: ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein B - John E. Bartmess

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 + C5H8 = C5H10

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-112.7 ± 0.54	kJ/mol	Chyd	Allinger, Dodziuk, et al., 1982	liquid phase; solvent: Hexane; ALS
ΔrH°	-112. ± 0.8	kJ/mol	Chyd	Roth and Lennartz, 1980	liquid phase; solvent: Cyclohexane; ALS
ΔrH°	-109.0 ± 1.8	kJ/mol	Chyd	Turner, Jarrett, et al., 1973	liquid phase; solvent: Acetic acid; ALS
ΔrH°	-110. ± 0.8	kJ/mol	Chyd	Rogers and McLafferty, 1971	liquid phase; solvent: Hydrocarbon; ALS
ΔrH°	-111.6 ± 0.3	kJ/mol	Chyd	Dolliver, Gresham, et al., 1937	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -112.6 ± 0.3 kJ/mol; At 355 °K; ALS

C5H9- + =

By formula: C5H9- + H+ = C5H10

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	1741. ± 8.4	kJ/mol	Bran	DePuy, Gronert, et al., 1989	gas phase; B
ΔrH°	1750. ± 8.4	kJ/mol	Bran	Peerboom, Rademaker, et al., 1992	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
ΔrG°	1705. ± 8.8	kJ/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase; B
ΔrG°	1714. ± 8.8	kJ/mol	H-TS	Peerboom, Rademaker, et al., 1992	gas phase; B

+ =

By formula: H2 + C5H8 = C5H10

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-235. ± 0.4	kJ/mol	Chyd	Roth, Klarner, et al., 1980	liquid phase; solvent: Heptane; ALS
ΔrH°	-230.7 ± 1.5	kJ/mol	Chyd	Turner, Goebel, et al., 1968	liquid phase; solvent: Acetic acid; ALS

2 + =

By formula: 2H2 + C5H6 = C5H10

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-210.8 ± 0.84	kJ/mol	Chyd	Kistiakowsky, Ruhoff, et al., 1936	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -212.8 ± 0.84 kJ/mol; At 355 °K; ALS

2 + =

By formula: 2H2 + C5H6 = C5H10

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-410. ± 2.	kJ/mol	Chyd	Roth, Klarner, et al., 1980	liquid phase; solvent: Heptane; ALS

+ = 2 +

By formula: C5H10 + I2 = 2HI + C5H8

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	102.1	kJ/mol	Eqk	Furuyama, Golden, et al., 1970	gas phase; ALS

References

Go To: Top, 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.

Spitzer and Huffman, 1947 Spitzer, R.; Huffman, H.M., The heats of combustion of cyclopentane, cyclohexane, cycloheptane and cyclooctane, J. Am. Chem. Soc., 1947, 69, 211-213. [all data]

Prosen, Johnson, et al., 1946 Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heats of formation and combustion of the normal alkylcyclopentanes and cyclohexanes and the increment per CH2 group for several homologous series of hydrocarbons, J. Res. NBS, 1946, 37, 51-56. [all data]

Kaarsemaker and Coops, 1952 Kaarsemaker, S.; Coops, J., Thermal quantities of some cycloparaffins. Part III. Results of measurements, Rec. Trav. Chim. Pays/Bas, 1952, 71, 261. [all data]

Douslin and Huffman, 1946 Douslin, D.R.; Huffman, H.M., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentane, methylcyclopentane and methylcylohexane, J. Am. Chem. Soc., 1946, 68, 173-176. [all data]

Aston, Fink, et al., 1943 Aston, J.G.; Fink, H.L.; Schumann, S.C., The heat capacity and entropy, heats of transition, fusion and vaporization and the vapor pressures of cyclopentane. Evidence for a non-planar structure, J. Am. Chem. Soc., 1943, 65, 341-346. [all data]

Jacobs and Parks, 1934 Jacobs, C.J.; Parks, G.S., Thermal data on organic compounds. XIV. Some heat capacity, entropy and free energy data for cyclic substances, J. Am. Chem. Soc., 1934, 56, 1513-1517. [all data]

Tanaka, 1985 Tanaka, R., Excess heat capacities for mixtures of benzene with cyclopentane, methylcyclohexane, and cyclooctane at 298.15 K, J. Chem. Eng. Data, 1985, 30, 267-269. [all data]

Siddiqi, Svejda, et al., 1983 Siddiqi, M.A.; Svejda, P.; Kohler, F., A generalized van der Waals equation of state II. Excess heat capacities of mixtures containing cycloalkanes (C5,C6), methylcycloalkanes (C5,C6) and n-decane, Ber. Bunsenges. Phys. Chem., 1983, 87, 1176-1181. [all data]

Fortier, D'Arcy, et al., 1979 Fortier, J.-L.; D'Arcy, P.J.; Benson, G.C., Heat capacities of binary cycloalkane mixtures at 298.15 K, Thermochim. Acta, 1979, 28, 37-43. [all data]

Jolicoeur, Boileau, et al., 1975 Jolicoeur, C.; Boileau, J.; Bazinet, S.; Picker, P., Thermodynamic properties of aqueous organic solutes in relation to their structure. Part II. Apparent molal volumes and heat capacities of c-alkylamine hydrobromides in water, Can. J. Chem., 1975, 53, 716-722. [all data]

Szasz, Morrison, et al., 1947 Szasz, G.J.; Morrison, J.A.; Pace, E.L.; Aston, J.G., Thermal properties of cyclopentane and its use as a standard substance in low temperature thermal measurements, J. Chem. Phys., 1947, 15, 562-564. [all data]

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]

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]

DePuy, Gronert, et al., 1989 DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Peerboom, Rademaker, et al., 1992 Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]

Roth, Klarner, et al., 1980 Roth, W.R.; Klarner, F.-G.; Lennartz, H.-W., Heats of hydrogenation. II. Heat of hydrogenation of bicyclo[2.1.0]pent-2-ene, an antiaromatic system, Chem. Ber., 1980, 113, 1806-1818. [all data]

Turner, Goebel, et al., 1968 Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M., Heats of hydrogenation. VIII. Compounds with three- and four-membered rings, J. Am. Chem. Soc., 1968, 90, 4315-4322. [all data]

Kistiakowsky, Ruhoff, et al., 1936 Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene, J. Am. Chem. Soc., 1936, 58, 146-153. [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]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References

• Symbols used in this document:

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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