Acepentalene

Acepentalene

Names
IUPAC name Cyclopenta[cd]pentalene
Other names Acepentylene
Identifiers
CAS Number	187-68-8
3D model (Jmol)	Interactive image Interactive image
ChemSpider	21477342
InChI InChI=1S/C10H6/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-6H Key: CUIAUPQXSDOJAG-UHFFFAOYSA-N InChI=1/C10H6/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-6H Key: CUIAUPQXSDOJAG-UHFFFAOYAJ
SMILES C2(C=C3)=C1C3=CC=C1C=C2 C1=CC2=CC=C3C2=C1C=C3
Properties
Chemical formula	C10H6
Molar mass	126.16 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acepentalene is a tricyclic anti-aromatic compound. Its molecular formula is C₁₀H₆. It consists of three five-membered rings fused across three of the five carbon atoms. The central carbon atom in acepentalene is part of all three rings. There are formally five double bonds in acepentalene, so that the molecule formally contains four double bonds on the exterior, and one double bond from the central carbon to the exterior of the ring system.

The acepentalene dianion, which can be stabilized by two lithium atoms, is more stable. The radical anion is also known.^[1]

References

1. Armin de Meijere; Fabian Gerson; Peter R. Schreiner; Pascal Merstetter; Franz-Manfred Schüngel (1999). "The radical anion of acepentalene". Chem. Commun.: 2189–2190. doi:10.1039/a906972k.