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
The 3d structure may be viewed using Java or Javascript. - 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 compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 19. ± 6. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
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 | 10.4 ± 0.48 | kcal/mol | Ccb | Steele, 1978 | ALS |
| ΔfH°liquid | 5.74 ± 0.52 | kcal/mol | Ccb | Hall, Smith, et al., 1973 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1010.3 ± 0.48 | kcal/mol | Ccb | Steele, 1978 | Corresponding ΔfHºliquid = 10.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1005.68 ± 0.52 | kcal/mol | Ccb | Hall, Smith, et al., 1973 | Corresponding ΔfHºliquid = 5.75 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔfH°solid | 7.42 ± 0.27 | kcal/mol | Ccb | Kozina, Bychikhina, et al., 1976 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1007.36 ± 0.24 | kcal/mol | Ccb | Kozina, Bychikhina, et al., 1976 | Corresponding ΔfHºsolid = 7.43 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 30.83 | 298.15 | Steele, 1978 | DH |
| 26.34 | 297. | Hall, Smith, et al., 1973 | DH |
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:
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 |
|---|---|---|---|---|---|
| ΔvapH° | 9.20 | kcal/mol | N/A | Osmont, Catoire, et al., 2008 | AC |
| ΔvapH° | 9.2 ± 0.2 | kcal/mol | C | Steele, 1978 | ALS |
| ΔvapH° | 9.25 | kcal/mol | N/A | Steele, 1978 | DRB |
| ΔvapH° | 9.08 ± 0.02 | kcal/mol | V | Hall, Smith, et al., 1973 | ALS |
| ΔvapH° | 9.08 | kcal/mol | N/A | Hall, Smith, et al., 1973 | DRB |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 9.2 ± 0.2 | kcal/mol | BG | Steele, 1978 | AC |
| ΔsubH° | 9.37 ± 0.26 | kcal/mol | C | Kozina, Bychikhina, et al., 1976, 2 | AC |
| ΔsubH° | 9.36 ± 0.26 | kcal/mol | V | Kozina, Bychikhina, et al., 1976 | ALS |
| ΔsubH° | 9.37 | kcal/mol | N/A | Kozina, Bychikhina, et al., 1976 | DRB |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 9.15 | 317. | A | Stephenson and Malanowski, 1987 | Based on data from 302. to 337. K.; AC |
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 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
+
=
By formula: H2 + C7H10 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -31.1 ± 0.2 | kcal/mol | Chyd | Flury, Grob, et al., 1988 | liquid phase; solvent: Isooctane |
| ΔrH° | -32.58 ± 0.52 | kcal/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values |
Gas phase ion energetics 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C7H10+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.7 | PE | Della, Pigou, et al., 1985 | LBLHLM |
| 8.92 ± 0.01 | EI | Holmes and McGillivray, 1971 | LLK |
| 9.02 | PE | Bodor, Dewar, et al., 1970 | RDSH |
| 9.37 | PE | Della, Pigou, et al., 1985 | Vertical value; LBLHLM |
| 9.40 | PE | Haselbach, Heilbronner, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C5H6+ | 9.44 ± 0.01 | C2H4 | EI | Holmes and McGillivray, 1971 | LLK |
| C6H7+ | 10.17 ± 0.01 | CH3 | EI | Holmes and McGillivray, 1971 | LLK |
| C7H9+ | 11.3 ± 0.01 | H | EI | Holmes and McGillivray, 1971 | LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Della, Pigou, et al., 1985
Della, E.W.; Pigou, P.E.; Livett, M.K.; Peel, J.B.,
The photoelectron spectrum of 1-bromotricyclene,
Aust. J. Chem., 1985, 38, 69. [all data]
Holmes and McGillivray, 1971
Holmes, J.L.; McGillivray, D.,
The mass spectra of isomeric hydrocarbons-I: Norbornene and nortricyclene; The mechanisms and energetics of their fragmentations,
Org. Mass Spectrom., 1971, 5, 1349. [all data]
Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method,
J. Am. Chem. Soc., 1970, 92, 19. [all data]
Haselbach, Heilbronner, et al., 1972
Haselbach, E.; Heilbronner, E.; Musso, H.; Schmelzer, A.,
Notiz uber die Photoelektronen-Spektren des Nortricyclens und des Triasterans,
Helv. Chim. Acta, 1972, 55, 302. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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