[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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Condensed phase thermochemistry data
Go To: Top, 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, 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]
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, 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°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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