Cycloheptane

Formula: C₇H₁₄
Molecular weight: 98.1861
IUPAC Standard InChI: InChI=1S/C7H14/c1-2-4-6-7-5-3-1/h1-7H2
IUPAC Standard InChIKey: DMEGYFMYUHOHGS-UHFFFAOYSA-N
CAS Registry Number: 291-64-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Gas phase thermochemistry data

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Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
S°_gas	342.3 ± 1.3	J/mol*K	N/A	Finke H.L., 1956

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
37.94	50.	Dorofeeva O.V., 1986	Discrepancies between recommended Cp(T) values and those calculated by molecular mechanics method [ Chang S., 1970] amount to 3.6-7.7 J/molK; discrepancies in S(T) values increase at high temperatures up to 2.3 J/molK for 500 K.
52.13	100.
68.39	150.
86.84	200.
119.63	273.15
132.0 ± 3.5	298.15
132.94	300.
183.23	400.
228.47	500.
266.45	600.
298.03	700.
324.49	800.
346.86	900.
365.89	1000.
382.13	1100.
396.04	1200.
407.99	1300.
418.28	1400.
427.19	1500.

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	-156.4 ± 1.7	kJ/mol	Ccb	Spitzer and Huffman, 1947	Reanalyzed by Cox and Pilcher, 1970, Original value = -157.9 ± 2.3 kJ/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-4597.0 ± 0.8	kJ/mol	Ccb	Kozina, Skuratov, et al., 1961	Corresponding Δ_fHº_liquid = -159. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-4597.6 ± 0.6	kJ/mol	Ccb	Kaarsemaker and Coops, 1952	Corresponding Δ_fHº_liquid = -157.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-4598.9 ± 1.7	kJ/mol	Ccb	Spitzer and Huffman, 1947	Reanalyzed by Cox and Pilcher, 1970, Original value = -4598.6 ± 1.7 kJ/mol; Corresponding Δ_fHº_liquid = -156.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-4586.5	kJ/mol	Ccb	Zubova, 1901	Corresponding Δ_fHº_liquid = -169. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	242.55	J/mol*K	N/A	Finke, Scott, et al., 1956	DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
180.614	298.15	Fortier, D'Arcy, et al., 1979	DH
180.47	298.15	Jolicoeur, Boileau, et al., 1975	DH
180.75	298.15	Finke, Scott, et al., 1956	T = 12 to 300 K.; DH

Reaction thermochemistry data

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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

+ = Cycloheptane

By formula: H₂ + C₇H₁₂ = C₇H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-110. ± 0.4	kJ/mol	Chyd	Roth and Lennartz, 1980	liquid phase; solvent: Cyclohexane; ALS
Δ_rH°	-108.2 ± 0.4	kJ/mol	Chyd	Turner, Meador, et al., 1957	liquid phase; solvent: Acetic acid; ALS
Δ_rH°	-108.9 ± 0.63	kJ/mol	Chyd	Conn, Kistiakowsky, et al., 1939	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -111.0 ± 0.08 kJ/mol; At 355 K; ALS

3 + = Cycloheptane

By formula: 3H₂ + C₇H₈ = C₇H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-305. ± 0.4	kJ/mol	Chyd	Roth, Klaerner, et al., 1983	liquid phase; solvent: Isooctane; ALS
Δ_rH°	-294.9 ± 1.6	kJ/mol	Chyd	Turner, Meador, et al., 1957	liquid phase; solvent: Acetic acid; ALS
Δ_rH°	-301.7 ± 1.3	kJ/mol	Chyd	Conn, Kistiakowsky, et al., 1939	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -304.8 ± 0.04 kJ/mol; at 355 K; ALS

2 + = Cycloheptane

By formula: 2H₂ + C₇H₁₀ = C₇H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-208.9 ± 0.3	kJ/mol	Chyd	Turner, Mallon, et al., 1973	liquid phase; solvent: Glacial acetic acid; ALS
Δ_rH°	-212.4 ± 0.63	kJ/mol	Chyd	Conn, Kistiakowsky, et al., 1939	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -214.5 ± 0.2 kJ/mol; At 355 K; ALS

C₇H₁₃^- + = Cycloheptane

By formula: C₇H₁₃^- + H⁺ = C₇H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1739. ± 20.	kJ/mol	Bran	Peerboom, Rademaker, et al., 1992	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1702. ± 21.	kJ/mol	H-TS	Peerboom, Rademaker, et al., 1992	gas phase; B

2 + = Cycloheptane

By formula: 2H₂ + C₇H₁₀ = C₇H₁₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-234. ± 3.	kJ/mol	Chyd	Turner, Mallon, et al., 1973	liquid phase; solvent: Glacial acetic acid; ALS

References

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Finke H.L., 1956
Finke H.L., Cycloheptane, cyclooctane, and 1,3,5-cycloheptatriene. Low-temperature thermal properties, vapor pressure, and derived chemical thermodynamic properties, J. Am. Chem. Soc., 1956, 78, 5469-5476. [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]

Chang S., 1970
Chang S., The heats of combustion and strain energies of bicyclo[n.m.0]alkanes, J. Am. Chem. Soc., 1970, 92, 3109-3118. [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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Kozina, Skuratov, et al., 1961
Kozina, M.P.; Skuratov, S.M.; Shtekher, S.M.; Sosnina, I.E.; Turova-Polyak, M.B., Heats of combustion of some bicyclanes, Russ. J. Phys. Chem. (Engl. Transl.), 1961, 35, 1144-1146. [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]

Zubova, 1901
Zubova, P., Data about heat of combustion of compound cycle structure, Zh. Fiz. Khim., 1901, 33, 708-722. [all data]

Finke, Scott, et al., 1956
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G., Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties, J. Am. Chem. Soc., 1956, 78, 5469-5476. [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]

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, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Winkler, R.E., Heats of hydrogenation. I. Apparatus and the heats of hydrogenation of bicyclo[2,2,1]heptene, bicyclo[2,2,1]heptadiene, bicyclo[2,2,2]octene and bicyclo[2,2,2]octadiene, J. Am. Chem. Soc., 1957, 79, 4116-4121. [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [all data]

Roth, Klaerner, et al., 1983
Roth, W.R.; Klaerner, F.G.; Gerit, F.; Grimme, W.; Koeser, H.G.; Busch, R.; Muskulus, B.; Breuckmann, R.; Scholz, B.P.; Lennartz, H.W., Stereochemistry of the bicyclo[2.1.0]pentane ring opening: thermolysis of tricyclo[3.2.0.0(,)]heptane derivatives, Chem. Ber., 1983, 116, 2717-2737. [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]

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]

Notes

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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°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rG°	Free energy of reaction 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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