Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane
- Formula: C7H8
- Molecular weight: 92.1384
- IUPAC Standard InChIKey: DGZUEIPKRRSMGK-UHFFFAOYSA-N
- CAS Registry Number: 278-06-8
- 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: [2.2.1.02,6.03,5]Quadricycloheptane; Quadricyclane; Tetracyclo[2.2.1.0(2,6).0(3,5)]heptane; tetracyclo[2.2.1.02,6.03,5]heptane
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, References, Notes
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 | 302.1 ± 2.2 | kJ/mol | Ccb | Steele, 1978 | ALS |
ΔfH°liquid | 216.3 ± 1.1 | kJ/mol | Ccb | Hall, Smith, et al., 1973 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4200.0 ± 2.2 | kJ/mol | Ccb | Steele, 1978 | Corresponding ΔfHºliquid = 302.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -4114.3 ± 1.1 | kJ/mol | Ccb | Hall, Smith, et al., 1973 | Corresponding ΔfHºliquid = 216.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
157.6 | 298.15 | Steele, 1978 | DH |
139.1 | 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:
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔvapH° | 37.3 ± 0.8 | kJ/mol | AVG | N/A | Average of 8 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
381.2 | 0.987 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
37.3 ± 0.8 | 317. | BG | Stephenson and Malanowski, 1987 | Based on data from 302. to 372. K. See also Hall, Smith, et al., 1973.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.09 | 228. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
40. | 180. | Domalski and Hearing, 1996 | CAL |
4.8 | 228. |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
180. | crystaline, II | crystaline, I | Kawai, Gilson, et al., 1992 | S = 40.0 J/mol*K; DH |
228. | crystaline, I | liquid | Kawai, Gilson, et al., 1992 | S = 4.8 J/mol*K; DH |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, References, Notes
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: C7H8 = C7H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -90. ± 30. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
C7H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1686. ± 4.2 | kJ/mol | D-EA | Gunion, Karney, et al., 1996 | gas phase; Assignment of 1- and 2- isomers uncertain.; B |
ΔrH° | 1685.6 ± 3.8 | kJ/mol | G+TS | Lee, DePuy, et al., 1996 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1651.4 ± 3.3 | kJ/mol | IMRE | Lee, DePuy, et al., 1996 | gas phase; B |
By formula: 2H2 + C7H8 = C7H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -384.7 ± 1.8 | kJ/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane; ALS |
ΔrH° | -385.1 ± 2.1 | kJ/mol | Chyd | Turner, Goebel, et al., 1968 | liquid phase; solvent: Acetic acid; ALS |
C7H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1685.7 ± 3.8 | kJ/mol | G+TS | Lee, DePuy, et al., 1996 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1651.4 ± 3.3 | kJ/mol | IMRE | Lee, DePuy, et al., 1996 | gas phase; B |
By formula: C7H8 = C7H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 59. ± 4. | kJ/mol | Ciso | Harel, Adamson, et al., 1987 | liquid phase; solvent: Cyclohexane; Photocalorimetry; ALS |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]
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]
Kawai, Gilson, et al., 1992
Kawai, N.T.; Gilson, D.F.R.; Butler, I.S.,
The order-disorder phase transition in the cage hydrocarbon quadricyclane, Mol. Cryst. Liq. Cryst. Sci. Technol.,
Sect., 1992, A 211, 59-61. [all data]
Gunion, Karney, et al., 1996
Gunion, R.F.; Karney, W.; Wenthold, P.G.; Borden, W.T.; Lineberger, W.C.,
Ultraviolet Photoelectron Spectroscopy of Some C7H7- Isomers: Quadricyclanide, Norbornadienide, Cycloheptatrienide, and 1,6-Heptadiynide,
J. Am. Chem. Soc., 1996, 118, 21, 5074, https://doi.org/10.1021/ja954026f
. [all data]
Lee, DePuy, et al., 1996
Lee, H.S.; DePuy, C.H.; Bierbaum, V.M.,
Reactivity and Thermochemistry of Quadricyclane in the Gas Phase,
J. Am. Chem. Soc., 1996, 118, 21, 5068, https://doi.org/10.1021/ja9540278
. [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]
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]
Harel, Adamson, et al., 1987
Harel, Y.; Adamson, A.W.; Kutal, C.; Grutsch, P.A.; Yasufuku, K.,
Photocalorimetry. 6. Enthalpies of isomerization of norbornadiene and of substituted norbornadienes to corresponding quadricyclenes,
J. Phys. Chem., 1987, 91, 901-904. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point Ttrs Temperature of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction 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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