Tricyclo[2.2.1.0(2,6)]heptane

Formula: C₇H₁₀
Molecular weight: 94.1543
IUPAC Standard InChI: InChI=1S/C7H10/c1-4-2-6-5(1)7(6)3-4/h4-7H,1-3H2
IUPAC Standard InChIKey: BYBGSCXPMGPLFP-UHFFFAOYSA-N
CAS Registry Number: 279-19-6
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Nortricyclane; Nortricyclen; Nortricyclene; Tricyclo[2.2.1.0dimethyl2dimethyl,dimethyl6]heptane; Tricyclo[2.2.1.0(2.6)]heptane; Tricyclo[2.2.1.0^2^,^6]heptane
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Gas 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_fH°_gas	80. ± 20.	kJ/mol	AVG	N/A	Average of 6 values; Individual data points

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	43.4 ± 2.0	kJ/mol	Ccb	Steele, 1978	ALS
Δ_fH°_liquid	24.0 ± 2.2	kJ/mol	Ccb	Hall, Smith, et al., 1973	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-4227.1 ± 2.0	kJ/mol	Ccb	Steele, 1978	Corresponding Δ_fHº_liquid = 43.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-4207.8 ± 2.2	kJ/mol	Ccb	Hall, Smith, et al., 1973	Corresponding Δ_fHº_liquid = 24.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	31.0 ± 1.1	kJ/mol	Ccb	Kozina, Bychikhina, et al., 1976	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-4214.8 ± 1.0	kJ/mol	Ccb	Kozina, Bychikhina, et al., 1976	Corresponding Δ_fHº_solid = 31.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
129.0	298.15	Steele, 1978	DH
110.2	297.	Hall, Smith, et al., 1973	DH

Phase change data

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Data compiled as indicated in comments:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	38.5	kJ/mol	N/A	Osmont, Catoire, et al., 2008	AC
Δ_vapH°	38.7 ± 0.7	kJ/mol	C	Steele, 1978	ALS
Δ_vapH°	38.7	kJ/mol	N/A	Steele, 1978	DRB
Δ_vapH°	38.0 ± 0.08	kJ/mol	V	Hall, Smith, et al., 1973	ALS
Δ_vapH°	38.0	kJ/mol	N/A	Hall, Smith, et al., 1973	DRB
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	38.7 ± 0.7	kJ/mol	BG	Steele, 1978	AC
Δ_subH°	39.2 ± 1.1	kJ/mol	C	Kozina, Bychikhina, et al., 1976, 2	AC
Δ_subH°	39.2 ± 1.1	kJ/mol	V	Kozina, Bychikhina, et al., 1976	ALS
Δ_subH°	39.2	kJ/mol	N/A	Kozina, Bychikhina, et al., 1976	DRB

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
38.3	317.	A	Stephenson and Malanowski, 1987	Based on data from 302. to 337. K.; AC

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

+ Tricyclo[2.2.1.0(2,6)]heptane =

By formula: H₂ + C₇H₁₀ = C₇H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-130. ± 0.8	kJ/mol	Chyd	Flury, Grob, et al., 1988	liquid phase; solvent: Isooctane
Δ_rH°	-136.3 ± 2.2	kJ/mol	Chyd	Rogers, Choi, et al., 1980	liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values

References

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Steele, 1978
Steele, W.V., The standard enthalpies of formation of a series of C₇, bridged-ring hydrocarbons: norbornane, norbornene, nortricyclene, norbornadiene, and quadricyclane, J. Chem. Thermodyn., 1978, 10, 919-927. [all data]

Hall, Smith, et al., 1973
Hall, H.K., Jr.; Smith, C.D.; Baldt, J.H., Enthalpies of formation of norticyclene, norbornene, norbornadiene, and quadricyclane, J. Am. Chem. Soc., 1973, 95, 3197-3201. [all data]

Kozina, Bychikhina, et al., 1976
Kozina, M.P.; Bychikhina, L.V.; Gal'chenko, G.L.; Mil'vitskaya, E.M.; Ordubadi, M.; Plate, A.F., Enthalpies of nortricyclene and norbornene formation, Dokl. Akad. Nauk SSSR, 1976, 226, 1105-1108. [all data]

Osmont, Catoire, et al., 2008
Osmont, Antoine; Catoire, Laurent; Gokalp, Iskender, Physicochemical Properties and Thermochemistry of Propellanes, Energy Fuels, 2008, 22, 4, 2241-2257, https://doi.org/10.1021/ef8000423 . [all data]

Kozina, Bychikhina, et al., 1976, 2
Kozina, M.P.; Bychikhina, L.V.; Gal'chenko, G.V.; Milwitskaya, E.M.; Ordubade, M.; Plate, A.F., Dokl. Akad. Nauk SSSR, 1976, 226, 1105. [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]

Flury, Grob, et al., 1988
Flury, P.; Grob, C.A.; Wang, G.Y.; Lennatz, H.-W.; Roth, W.R., 113. Norbornanes. Bridging strain in norbornyl and oxanorbornyl cations, Helv. Chim. Acta, 1988, 71, 1017-1024. [all data]

Rogers, Choi, et al., 1980
Rogers, D.W.; Choi, L.S.; Girellini, R.S., Heats of hydrogenation and formation of quadricyclene, norbornadiene, norbornene, and nortricyclene, J. Phys. Chem., 1980, 84, 1810-1814. [all data]

Notes

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Symbols used in this document:

C_p,solid	Constant pressure heat capacity of solid
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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