(2.2)Metacyclophane
- Formula: C16H16
- Molecular weight: 208.2982
- IUPAC Standard InChI: InChI=1S/C16H16/c1-3-13-7-9-15-5-2-6-16(12-15)10-8-14(4-1)11-13/h1-6,11-12H,7-10H2
- IUPAC Standard InChIKey: COTONUHLIMVDNV-UHFFFAOYSA-N
- CAS Registry Number: 2319-97-3
- 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[9.3.1.1<sup>4,8</sup>]hexadeca-1(15),4,6,8(16),11,13-hexaene; Di-m-xylylene; Di-1,3-xylylene; Tricyclo(9.3.1.14,8)hexadeca-1(15),4,6,8(16),11,13-hexaene; Triple-layered-(2.2)metacyclophane
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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔsubH° | 92. ± 2. | kJ/mol | V | Shieh, McNally, et al., 1969 | ALS |
| ΔsubH° | 91.8 | kJ/mol | N/A | Shieh, McNally, et al., 1969 | DRB |
| ΔsubH° | 92. ± 2. | kJ/mol | ME | Shieh, McNally, et al., 1969 | See also Pedley and Rylance, 1977.; AC |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 91.6 ± 1.7 | 320. | ME | Shieh, McNally, et al., 1969 | Based on data from 308. to 332. K. See also Pedley and Rylance, 1977 and Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 21.42 | 404. | Shieh, McNally, et al., 1969 | AC |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J.,
, Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [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]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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