Cyclodecane

Formula: C₁₀H₂₀
Molecular weight: 140.2658
IUPAC Standard InChI: InChI=1S/C10H20/c1-2-4-6-8-10-9-7-5-3-1/h1-10H2
IUPAC Standard InChIKey: LMGZGXSXHCMSAA-UHFFFAOYSA-N
CAS Registry Number: 293-96-9
Chemical structure:
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Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1574.1 ± 0.2	kcal/mol	Ccb	Coops, Van Kamp, et al., 1960	Corresponding Δ_fHº_liquid = -49.52 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_liquid	-1577.5 ± 1.5	kcal/mol	Ccb	Huckel, Gercke, et al., 1933	Corresponding Δ_fHº_liquid = -46.16 kcal/mol (simple calculation by NIST; no Washburn corrections)

Reaction thermochemistry data

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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

2 + = Cyclodecane

By formula: 2H₂ + C₁₀H₁₆ = C₁₀H₂₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-56.46 ± 0.23	kcal/mol	Chyd	Turner, Jarrett, et al., 1973	liquid phase; solvent: Acetic acid
Δ_rH°	-56.5	kcal/mol	Chyd	Sicher, Svoboda, et al., 1966	liquid phase; solvent: Acetic acid

2 + = Cyclodecane

By formula: 2H₂ + C₁₀H₁₆ = C₁₀H₂₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-47.63	kcal/mol	Chyd	Turner, Mallon, et al., 1973	liquid phase; solvent: Glacial acetic acid

+ 2 = Cyclodecane

By formula: C₁₀H₁₆ + 2H₂ = C₁₀H₂₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-43.73	kcal/mol	Chyd	Turner, Mallon, et al., 1973	liquid phase; solvent: Glacial acetic acid

+ = Cyclodecane

By formula: H₂ + C₁₀H₁₈ = C₁₀H₂₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-20.67 ± 0.08	kcal/mol	Chyd	Turner and Meador, 1957	liquid phase; solvent: Acetic acid

+ = Cyclodecane

By formula: H₂ + C₁₀H₁₈ = C₁₀H₂₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-24.0 ± 0.9	kcal/mol	Chyd	Turner and Meador, 1957	liquid phase; solvent: Acetic acid

4 + = Cyclodecane

By formula: 4H₂ + C₁₀H₁₂ = C₁₀H₂₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-123.0 ± 0.2	kcal/mol	Chyd	Roth, Adamczak, et al., 1991	liquid phase

References

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

Coops, Van Kamp, et al., 1960
Coops, J.; Van Kamp, H.; Lambregts, W.A.; Visser, B.J.; Dekker, H., Thermal quantities of cycloparaffins. Part IV. Heats of combustion of cycloparaffins with 10-17 C atoms, Rec. Trav. Chim. Pays/Bas, 1960, 79, 1226-1234. [all data]

Huckel, Gercke, et al., 1933
Huckel, W.; Gercke, A.; Gross, A., Cyclodecan, Ber., 1933, 66, 563-567. [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]

Sicher, Svoboda, et al., 1966
Sicher, J.; Svoboda, M.; Zavada, J.; Turner, R.B.; Goebel, P., Sterochemical studies - XXXVI. An approach to conformational analysis of medium ring compounds. Unsaturated ten-membered ring derivates, Tetrahedron, 1966, 22, 659-671. [all data]

Turner, Mallon, et al., 1973
Turner, R.B.; Mallon, B.J.; Tichy, M.; Doering, W.v.E.; Roth, W.R.; Schroder, G., Heats of hydrogenation. X. Conjugative interaction in cyclic dienes and trienes, J. Am. Chem. Soc., 1973, 95, 8605-8610. [all data]

Turner and Meador, 1957
Turner, R.B.; Meador, W.R., Heats of hydrogenation. IV. Hydrogenation of some cis- and trans-cycloolefins, J. Am. Chem. Soc., 1957, 79, 4133-4136. [all data]

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]

Notes

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Symbols used in this document:

Δ_cH°_liquid Enthalpy of combustion of liquid at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions