Bicalicene
Bicalicene is polycyclic hydrocarbon with chemical formula C16H8, composed of linked two cyclopentadiene ring and two cyclopropene ring.[1] There are two isomers: cis-bicalicene and trans-bicalicene.
Names | |
---|---|
IUPAC names
(4aZ,8aZ)-Dicyclopenta[a,e]dicyclopropa[c,g][8]annulene Dicyclopenta[a,e]dicyclopropa[c,g]cyclooctene | |
Identifiers | |
3D model (JSmol) |
|
ChemSpider | |
PubChem CID |
|
| |
| |
Properties | |
C16H8 | |
Molar mass | 200.240 g·mol−1 |
Melting point | 125-130°C (dec)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Names | |
---|---|
IUPAC name
Dicyclopenta[a,c]dicyclopropa[e,g]cyclooctene | |
Identifiers | |
3D model (JSmol) |
|
| |
Properties | |
C16H8 | |
Molar mass | 200.240 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Synthesis
Bicalicene is prepared by treatment of 1,2-bis(tert-butylthio)-3,3-dichlorocyclopropene with cyclopentadiene anion, followed by desulfurizing stannylation with tributyltin hydride and silica gel.[1]
Properties
trans-Bicalicene is polycyclic aromatic hydrocarbon with 16 pi electrons due to positive charge on the carbon atom of triangular ring and a negative charge on the carbon atom of pentagonal ring.[2]
cis-Bicalicene is an antiaromatic hydrocarbon.[3]
gollark: Macs ≈ Overpriced.
gollark: <@332271551481118732> http://kittenlang.org/intro/
gollark: Is RPNCalc (on my website) to have some sort of "execute N steps per second" mode?
gollark: Just make everything () unless specified otherwise.
gollark: Fascinating.
See also
References
- Yonedo S, Shibata M, Kida S, Yoshida Z, Kai Y, Miki K, Kasai N (January 1984). "A Novel Aromatic Hydrocarbon with 16π-Electron Periphery:"Cyclic Bicalicene"". Angewandte Chemie International Edition in English. 23 (1): 63–64. doi:10.1002/anie.198400631.
- Oziminski WP, Palusia M (2013). "Capturing the elusive aromaticity of bicalicene". Physical Chemistry Chemical Physics. 15: 3286–3293. doi:10.1039/C2CP43426A.
- Jelena Đurđević Nikolić; Ivan Gutman (2016). "A Comparative Study of the Two Isomers of Bicalicene". Polycyclic Aromatic Compounds: 1–7. doi:10.1080/10406638.2016.1140659.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.