[2.2]Paracyclophane
- Formula: C16H16
- Molecular weight: 208.2982
- IUPAC Standard InChI: InChI=1S/C16H16/c1-2-14-4-3-13(1)9-10-15-5-7-16(8-6-15)12-11-14/h1-8H,9-12H2
- IUPAC Standard InChIKey: OOLUVSIJOMLOCB-UHFFFAOYSA-N
- CAS Registry Number: 1633-22-3
- 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: Tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaene; Cyclobis(benzene-1,4-dimethylene); Di-p-xylylene; Di-1,4-xylylene; tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene
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Gas phase thermochemistry data
Go To: Top, Condensed phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 244.7 ± 2.1 | kJ/mol | Ccb | Nishiyama, Sakiyama, et al., 1980 | Reanalyzed by Cox and Pilcher, 1970, Original value = 246.3 ± 3.3 kJ/mol |
| ΔfH°gas | 241. ± 4.2 | kJ/mol | Ccb | Rodgers, Westrum, et al., 1973 | |
| ΔfH°gas | 241.3 ± 4.3 | kJ/mol | Ccb | Boyd, 1966 | Reanalyzed by Cox and Pilcher, 1970, Original value = 251. ± 7.9 kJ/mol |
Condensed phase thermochemistry data
Go To: Top, Gas phase 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°solid | 146.7 ± 2.8 | kJ/mol | Ccb | Nishiyama, Sakiyama, et al., 1980 | ALS |
| ΔfH°solid | 144.7 ± 0.88 | kJ/mol | Ccb | Rodgers, Westrum, et al., 1973 | ALS |
| ΔfH°solid | 154. ± 4. | kJ/mol | Ccb | Boyd, 1966 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -8729.5 ± 1.8 | kJ/mol | Ccb | Nishiyama, Sakiyama, et al., 1980 | Corresponding ΔfHºsolid = 146.68 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -8727.57 ± 0.63 | kJ/mol | Ccb | Rodgers, Westrum, et al., 1973 | Corresponding ΔfHºsolid = 144.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -8737. ± 4. | kJ/mol | Ccb | Boyd, 1966 | Corresponding ΔfHºsolid = 154. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 265.68 | J/mol*K | N/A | Andrews and Westrum, 1970 | DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 252.7 | 298.15 | Rodgers, Westrum, et al., 1973 | Cp given as 0.290 cal/g*K.; DH |
| 252.34 | 298.15 | Andrews and Westrum, 1970 | T = 10 to 350 K.; DH |
| 248.1 | 300. | Shieh, McNally, et al., 1969 | T = 300, 318 K.; DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Nishiyama, Sakiyama, et al., 1980
Nishiyama, K.; Sakiyama, N.; Seki, S.; Horita, H.; Otsubo, T.; Misumi, S.,
Thermochemical studies on double- and triple-layered [2.2]paracyclophanes. Estimation of molecular strain energies.,
Bull. Chem. Soc. Jpn., 1980, 53, 869-877. [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]
Rodgers, Westrum, et al., 1973
Rodgers, D.L.; Westrum, E.F., Jr.; Andrews, J.T.S.,
The enthalpies of combustion and formation of [2.2]-paracyclophane and triptycene,
J. Chem. Thermodyn., 1973, 5, 733-739. [all data]
Boyd, 1966
Boyd, R.H.,
The heat of combustion and strain energy of 2,2-paracyclophane,
Tetrahedron, 1966, 22, 119-122. [all data]
Andrews and Westrum, 1970
Andrews, J.T.S.; Westrum, E.F., Jr.,
The heat capacity and thermodynamic functions of crystalline and liquid triptycene,
J. Chem. Thermodynam., 1970, 2, 245-253. [all data]
Shieh, McNally, et al., 1969
Shieh, C.; McNally, D.; Boyd, R.H.,
The heats of combustion and strain energies of some cyclophanes,
Tetrahedron, 1969, 3653-3665. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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