聯杯烯

反-聯杯烯
IUPAC名
(4aZ,8aZ)-Dicyclopenta[a,e]dicyclopropa[c,g][8]annulene
Dicyclopenta[a,e]dicyclopropa[c,g]cyclooctene
识别
CAS号 73091-52-8  ☒N
PubChem 5257656
ChemSpider 4423214
SMILES
 
  • C1=CC2=C3C=C3C4=CC=CC4=C5C=C5C2=C1
InChI
 
  • 1/C16H8/c1-3-9-10(4-1)14-8-16(14)12-6-2-5-11(12)15-7-13(9)15/h1-8H/b13-9-,14-10-,15-11-,16-12-
InChIKey FVDGMBFXSFSQOU-NONDJZLBBM
性质
化学式 C16H8
摩尔质量 200.23 g·mol−1
熔点 125-130°C (dec)[1]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。
顺-聯杯烯
IUPAC名
Dicyclopenta[a,c]dicyclopropa[e,g]cyclooctene
识别
CAS号 122605-73-6  ☒N
SMILES
 
  • C1=CC2=C3C=C3C4=CC4=C5C=CC=C5C2=C1
性质
化学式 C16H8
摩尔质量 200.23 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

聯杯烯(Bicalicene)的分子式为C16H8。聯杯烯具有两个环丙烯环和两个环戊二烯环。整體的共軛體系包含16個π電子,理論上應為反芳香性。但反-聯杯烯的共振式可以出現帶正電的三元環和帶負電的五元環,各自符合休克爾規則,因而具有芳香性[2]而顺-聯杯烯同樣的共振式中相同電荷的環處於同側,是不穩定的,因此不具有芳香性,是不穩定的反芳香性化合物。[3]

参看

参考资料

  1. ^ Yonedo S, Shibata M, Kida S, Yoshida Zi, Kai Y, Miki K, Kasai N. A Novel Aromatic Hydrocarbon with 16π-Electron Periphery:"Cyclic Bicalicene". Angewandte Chemie International Edition in English. January 1984, 23 (1): 63–64. doi:10.1002/anie.198400631. 
  2. ^ Oziminski WP, Palusia M. Capturing the elusive aromaticity of bicalicene. Physical Chemistry Chemical Physics. 2013, 15: 3286–3293. doi:10.1039/C2CP43426A. 
  3. ^ Jelena Đurđević Nikolić; Ivan Gutman. A Comparative Study of the Two Isomers of Bicalicene. Polycyclic Aromatic Compounds. 2016: 1–7. doi:10.1080/10406638.2016.1140659. 

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