Cyclopentane

• Formula: C₅H₁₀
• Molecular weight: 70.1329
• IUPAC Standard InChI:
  

  InChI=1S/C5H10/c1-2-4-5-3-1/h1-5H2 Download the identifier in a file.

• IUPAC Standard InChIKey: RGSFGYAAUTVSQA-UHFFFAOYSA-N
• 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
  The 3d structure may be viewed using Java or Javascript.
• Other names: Pentamethylene; UN 1146
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Gas phase ion energetics data
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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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.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
fH°gas	-76.40 ± 0.79	kJ/mol	Ccb	McCullough, Pennington, et al., 1959	ALS
fH°gas	-76.9	kJ/mol	N/A	Spitzer and Huffman, 1947	Value computed using «DELTA»fHliquid° value of -105.6±1.8 kj/mol from Spitzer and Huffman, 1947 and «DELTA»vapH° value of 28.7 kj/mol from Prosen, Johnson, et al., 1946.; DRB
fH°gas	-77.24 ± 0.75	kJ/mol	Ccb	Prosen, Johnson, et al., 1946	ALS

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

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
fH°liquid	-105.6 ± 1.8	kJ/mol	Ccb	Spitzer and Huffman, 1947	ALS
fH°liquid	-105.9 ± 0.75	kJ/mol	Ccb	Prosen, Johnson, et al., 1946	ALS
Quantity	Value	Units	Method	Reference	Comment
cH°liquid	-3291.4 ± 0.6	kJ/mol	Ccb	Kaarsemaker and Coops, 1952	Corresponding «DELTA»fHºliquid = -105.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
cH°liquid	-3291.2 ± 1.3	kJ/mol	Ccb	Spitzer and Huffman, 1947	Corresponding «DELTA»fHºliquid = -105.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
cH°liquid	-3290.9 ± 0.71	kJ/mol	Ccb	Prosen, Johnson, et al., 1946	Corresponding «DELTA»fHºliquid = -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

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, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Tboil	322.4 ± 0.3	K	AVG	N/A	Average of 35 out of 40 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Tfus	179.2 ± 0.8	K	AVG	N/A	Average of 26 out of 28 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Ttriple	179.71	K	N/A	Douslin and Huffman, 1946, 2	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; To = 273.16 K; TRC
Ttriple	179.71	K	N/A	Douslin and Huffman, 1946, 2	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.007 K; To = 273.16 K; TRC
Ttriple	179.69	K	N/A	Aston, Finke, et al., 1943	Uncertainty assigned by TRC = 0.08 K; TRC
Ttriple	179.0	K	N/A	Jacobs and Parks, 1934, 2	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Tc	511.7 ± 0.2	K	N/A	Daubert, 1996
Tc	511.6	K	N/A	Majer and Svoboda, 1985
Tc	511.7	K	N/A	Kudchadker, Alani, et al., 1968	Uncertainty assigned by TRC = 0.2 K; TRC
Tc	511.6	K	N/A	Ambrose and Grant, 1957	Uncertainty assigned by TRC = 0.15 K; TRC
Tc	511.75	K	N/A	Kay, 1947	Uncertainty assigned by TRC = 0.05 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Pc	45.1 ± 0.4	bar	N/A	Daubert, 1996
Pc	45.08	bar	N/A	Kudchadker, Alani, et al., 1968	Uncertainty assigned by TRC = 0.4053 bar; TRC
Pc	44.30	bar	N/A	Ambrose and Grant, 1957	Uncertainty assigned by TRC = 0.5066 bar; TRC
Pc	45.1403	bar	N/A	Kay, 1947	Uncertainty assigned by TRC = 0.0506 bar; TRC
Quantity	Value	Units	Method	Reference	Comment
Vc	0.259	l/mol	N/A	Daubert, 1996
Quantity	Value	Units	Method	Reference	Comment
c	3.85 ± 0.04	mol/l	N/A	Daubert, 1996
c	3.850	mol/l	N/A	Kudchadker, Alani, et al., 1968	Uncertainty assigned by TRC = 0.06 mol/l; TRC
c	3.85	mol/l	N/A	Kay, 1947	Uncertainty assigned by TRC = 0.03 mol/l; TRC
Quantity	Value	Units	Method	Reference	Comment
vapH°	28.8 ± 0.6	kJ/mol	AVG	N/A	Average of 8 values; Individual data points

Enthalpy of vaporization

vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
27.3	322.4	N/A	Majer and Svoboda, 1985
29.213	298.15	N/A	Aston, Fink, et al., 1943	P = 41.10 kPa; DH
29.2	295.	A	Stephenson and Malanowski, 1987	Based on data from 280. - 331. K.; AC
28.0	337.	A	Stephenson and Malanowski, 1987	Based on data from 322. - 384. K.; AC
27.2	396.	A	Stephenson and Malanowski, 1987	Based on data from 381. - 455. K.; AC
27.5	467.	A	Stephenson and Malanowski, 1987	Based on data from 452. - 511. K.; AC
27.9 ± 0.1	310.	C	McCullough, Pennington, et al., 1959	AC
27.3 ± 0.1	322.	C	McCullough, Pennington, et al., 1959	AC
27.4	323.	N/A	Spitzer and Pitzer, 1946	AC
29.0	304.	MM	Willingham, Taylor, et al., 1945	Based on data from 289. - 323. K.; AC

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Temperature (K)	A (kJ/mol)		Tc (K)	Reference	Comment
298. - 323.	41.64	0.2597	511.6	Majer and Svoboda, 1985

Entropy of vaporization

vapS (J/mol*K)	Temperature (K)	Reference	Comment
97.98	298.15	Aston, Fink, et al., 1943	P; DH

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

subH (kJ/mol)	Temperature (K)	Method	Reference	Comment
42.6	122.	B	Bondi, 1963	AC

Enthalpy of fusion

fusH (kJ/mol)	Temperature (K)	Reference	Comment
0.6	179.7	Domalski and Hearing, 1996	AC

Enthalpy of phase transition

Htrs (kJ/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
5.195	121.95	crystaline, III	crystaline, II	Rahm and Gmelin, 1992	DH
0.361	138.22	crystaline, II	crystaline, I	Rahm and Gmelin, 1992	DH
0.615	179.21	crystaline, I	liquid	Rahm and Gmelin, 1992	DH
4.8844	122.36	crystaline, III	crystaline, II	Szasz, Morrison, et al., 1947	DH
0.3427	138.07	crystaline, II	crystaline, I	Szasz, Morrison, et al., 1947	Temperature from 43AST/FIN.; DH
0.6038	179.69	crystaline, I	liquid	Szasz, Morrison, et al., 1947	Temperature from 43AST/FIN.; DH
4.8840	122.39	crystaline, III	crystaline, II	Douslin and Huffman, 1946	DH
0.34443	138.09	crystaline, II	crystaline, I	Douslin and Huffman, 1946	DH
0.60894	179.71	crystaline, I	liquid	Douslin and Huffman, 1946	DH
4.874	122.39	crystaline, III	crystaline, II	Aston, Fink, et al., 1943	DH
0.3464	138.07	crystaline, II	crystaline, I	Aston, Fink, et al., 1943	DH
0.602	179.69	crystaline, I	liquid	Aston, Fink, et al., 1943	DH
4.745	121.6	crystaline, III	crystaline, II	Jacobs and Parks, 1934	DH
0.3582	137.1	crystaline, II	crystaline, I	Jacobs and Parks, 1934	DH
0.6046	179.0	crystaline, I	liquid	Jacobs and Parks, 1934	DH

Entropy of phase transition

Strs (J/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
39.92	122.36	crystaline, III	crystaline, II	Szasz, Morrison, et al., 1947	DH
2.48	138.07	crystaline, II	crystaline, I	Szasz, Morrison, et al., 1947	Temperature; DH
3.36	179.69	crystaline, I	liquid	Szasz, Morrison, et al., 1947	Temperature; DH
39.91	122.39	crystaline, III	crystaline, II	Douslin and Huffman, 1946	DH
2.49	138.09	crystaline, II	crystaline, I	Douslin and Huffman, 1946	DH
3.38	179.71	crystaline, I	liquid	Douslin and Huffman, 1946	DH
39.82	122.39	crystaline, III	crystaline, II	Aston, Fink, et al., 1943	DH
2.51	138.07	crystaline, II	crystaline, I	Aston, Fink, et al., 1943	DH
3.35	179.69	crystaline, I	liquid	Aston, Fink, et al., 1943	DH
39.02	121.6	crystaline, III	crystaline, II	Jacobs and Parks, 1934	DH
2.61	137.1	crystaline, II	crystaline, I	Jacobs and Parks, 1934	DH
3.38	179.0	crystaline, I	liquid	Jacobs and Parks, 1934	DH

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 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
rH°	-112.7 ± 0.54	kJ/mol	Chyd	Allinger, Dodziuk, et al., 1982	liquid phase; solvent: Hexane; ALS
rH°	-112. ± 0.8	kJ/mol	Chyd	Roth and Lennartz, 1980	liquid phase; solvent: Cyclohexane; ALS
rH°	-109.0 ± 1.8	kJ/mol	Chyd	Turner, Jarrett, et al., 1973	liquid phase; solvent: Acetic acid; ALS
rH°	-110. ± 0.8	kJ/mol	Chyd	Rogers and McLafferty, 1971	liquid phase; solvent: Hydrocarbon; ALS
rH°	-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
rH°	1741. ± 8.4	kJ/mol	Bran	DePuy, Gronert, et al., 1989	gas phase; B
rH°	1750. ± 8.4	kJ/mol	Bran	Peerboom, Rademaker, et al., 1992	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
rG°	1705. ± 8.8	kJ/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase; B
rG°	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
rH°	-235. ± 0.4	kJ/mol	Chyd	Roth, Klarner, et al., 1980	liquid phase; solvent: Heptane; ALS
rH°	-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
rH°	-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
rH°	-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
rH°	102.1	kJ/mol	Eqk	Furuyama, Golden, et al., 1970	gas phase; ALS

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); PERKIN-ELMER 180 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

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

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.

McCullough, Pennington, et al., 1959
McCullough, J.P.; Pennington, R.E.; Smith, J.C.; Hossenlopp, I.A.; Waddington, G., Thermodynamics of cyclopentane, methylcyclopentane and 1,cis-3-dimethylcyclopentane: Verification of the concept of pseudorotation, J. Am. Chem. Soc., 1959, 81, 5880-5883. [all data]

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]

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]

Kilpatrick J.E., 1947
Kilpatrick J.E., The thermodynamics and molecular structure of cyclopentane, J. Am. Chem. Soc., 1947, 69, 2483-2488. [all data]

McCullough J.P., 1959
McCullough J.P., Thermodynamics of cyclopentane, methylcyclopentane and 1,cis-3-dimethylcyclopentane: verification of the concept of pseudorotation, J. Am. Chem. Soc., 1959, 81, 5880-5883. [all data]

Sundaram S., 1963
Sundaram S., Thermodynamic functions of some propellants, Z. Phys. Chem. (Frankfurt), 1963, 36, 376-377. [all data]

Spitzer R., 1946
Spitzer R., The heat capacity of gaseous cyclopentane, cyclohexane and methylcyclohexane, J. Am. Chem. Soc., 1946, 68, 2537-2538. [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]

Douslin and Huffman, 1946, 2
Douslin, D.R.; Huffman, H.M., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentane, methylcyclopentane and methylcyclohexane., J. Am. Chem. Soc., 1946, 68, 173. [all data]

Aston, Finke, et al., 1943
Aston, J.G.; Finke, 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. [all data]

Jacobs and Parks, 1934, 2
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, 1513-17. [all data]

Daubert, 1996
Daubert, T.E., Vapor-Liquid Critical Properties of Elements and Compounds. 5. Branched Alkanes and Cycloalkanes, J. Chem. Eng. Data, 1996, 41, 365-372. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Kudchadker, Alani, et al., 1968
Kudchadker, A.P.; Alani, G.H.; Zwolinski, B.J., The Critical Constants of Organic Substances, Chem. Rev., 1968, 68, 659. [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]

Kay, 1947
Kay, W.B., Vapor Pressures and Saturated Liquid and Vapor DEensities of Cyclopentane, Methylcyclopentane, Ethylcyclopentane, and Methylcyclohexane, J. Am. Chem. Soc., 1947, 69, 1273-7. [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]

Spitzer and Pitzer, 1946
Spitzer, Ralph; Pitzer, Kenneth S., The Heat Capacity of Gaseous Cyclopentane, Cyclohexane and Methylcyclohexane, J. Am. Chem. Soc., 1946, 68, 12, 2537-2538, https://doi.org/10.1021/ja01216a032 . [all data]

Willingham, Taylor, et al., 1945
Willingham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor pressures and boiling points of some paraffin, alkylcyclopentane, alkylcyclohexane, and alkylbenzene hydrocarbons, J. RES. NATL. BUR. STAN., 1945, 35, 3, 219-17, https://doi.org/10.6028/jres.035.009 . [all data]

Williamham, Taylor, et al., 1945
Williamham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor Pressures and Boiling Points of Some Paraffin, Alkylcyclopentane, Alkylcyclohexane, and Alkylbenzene Hydrocarbons, J. Res. Natl. Bur. Stand. (U.S.), 1945, 35, 3, 219-244, https://doi.org/10.6028/jres.035.009 . [all data]

Bondi, 1963
Bondi, A., Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments., J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027 . [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]

Rahm and Gmelin, 1992
Rahm, U.; Gmelin, E., Low temperature microcalorimetry by differential scanning, J. Therm. Anal., 1992, 38(3), 335-344. [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

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• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  Htrs	Enthalpy of phase transition
  Strs	Entropy of phase transition
  cH°liquid	Enthalpy of combustion of liquid at standard conditions
  fH°gas	Enthalpy of formation of gas at standard conditions
  fH°liquid	Enthalpy of formation of liquid at standard conditions
  fusH	Enthalpy of fusion
  rG°	Free energy of reaction at standard conditions
  rH°	Enthalpy of reaction at standard conditions
  subH	Enthalpy of sublimation
  vapH	Enthalpy of vaporization
  vapH°	Enthalpy of vaporization at standard conditions
  vapS	Entropy of vaporization
  c	Critical density

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