Trithiapentalene

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Trithiapentalene
Trithiapentalene.svg
Trithiapentalene-from-xtal-3D-bs-17.png
Names
Preferred IUPAC name
4-[1,2]Dithiolo[1,5-b][1,2]dithiole
Systematic IUPAC name
4,2,8-Trithiabicyclo[3.3.0]octa-1(5),3,6-triene
Other names
1,6,6aλ4-Trithiapentalene, 6a-Thiothiophthene, 6a-Thiathiophthene
Identifiers
3D model (JSmol)
UNII
  • InChI=1S/C5H4S3/c1-3-6-8-5(1)2-4-7-8/h1-4H
    Key: JUEJPBZMWHMMPS-UHFFFAOYSA-N
  • C1=CSS2=C1C=CS2
Properties
C5H4S3
Molar mass 160.27 g·mol−1
Appearance Orange–red solid[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Trithiapentalene is an organic bicyclic molecule containing two sulfur heterocycles. Its 10-π aromatic structure is similar to naphthalene. There has been a literature dispute about whether the connectivity among the three sulfur atoms is a case of rapid tautomerization between two valence tautomers or a 3-center 4-electron bond.[2]

Resonance structures of trithiapentalene

The reactions have been little studied. It forms a dinickel complex upon reaction with bis(allyl)nickel.[3]

See also[edit]

References[edit]

  1. ^ Hansen, Lars K.; Hordvik, Asbjørn; Hebrew, C.; Buren, C. T. Van; Klæboe, P.; Swahn, Carl-Gunnar (1973). "The Crystal and Molecular Structure of 6a-Thiathiophthene". Acta Chemica Scandinavica. 27: 411–420. doi:10.3891/acta.chem.scand.27-0411.
  2. ^ Pedersen, Carl Th (1991-04-01). "The Structure of Trithiapentalenes and Related Compounds". Phosphorus, Sulfur, and Silicon and the Related Elements. 58 (1–4): 17–38. doi:10.1080/10426509108040624. ISSN 1042-6507.
  3. ^ Bogdanović, Borislav; Krüger, Carl; Kuzmin, Oleg (1979). "Bis(η3-allylnickel) 2,4,6-Heptanetrithionediate". Angewandte Chemie International Edition in English. 18 (9): 683–684. doi:10.1002/anie.197906831.