Thianthrene

Thianthrene
Names
IUPAC name
Thianthrene
Other names
Thianthren; 9,10-Dithiaanthracene; Di-o-phenylene disulfide
Identifiers
92-85-3 
ChEMBL ChEMBL488176 Yes
ChemSpider 6842 Yes
EC number 202-197-0
Jmol-3D images Image
PubChem 7109
Properties[1]
Molecular formula
 C12H8S2
Molar mass 216.32 g·mol−1
Melting point 151 °C (304 °F; 424 K)
Boiling point 364 °C (687 °F; 637 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Thianthrene is a sulfur-containing heterocyclic chemical compound. It is a derivative of the parent heterocycle called dithiin. It is notable for its ease of oxidation.

Structure and synthesis

Like other 1,4-dithiins but unlike its oxygen analog dibenzodioxin, the shape of thianthrene is not planar. It is bent, with a fold angle of 128° between the two benzo groups.[2][3][4]

Thianthrene can be prepared by treating benzene with disulfur dichloride in the presence of aluminium chloride.[5]

History

Thianthrene was first synthesized by John Stenhouse by dry distillation of sodium benzenesulfonate.[6] Thianthrene is oxidized by sulfuric acid forming a red radical cation.[7] Thianthrene•+ has been characterized by Electron paramagnetic resonance. Four different publications describe the crystal structure of salts of thianthrene•+.[8]

References

  1. ↑ Thianthrene at Sigma-Aldrich
  2. ↑ Hosoya, S. (1963). "Molecular shapes of thianthrene and related heterocyclic compounds". Acta Crystallographica 16 (4): 310–312. doi:10.1107/S0365110X63000797.
  3. ↑ Gallaher, K. L.; Bauer, S. H. (1975). "Structure and inversion potential of thianthren". Journal of the Chemical Society, Faraday Transactions 2 71: 1173–1182. doi:10.1039/F29757101173.
  4. ↑ Aroney, M. J.; Le Fèvre, R. J. W.; Saxby, J. D. (1965). "92. Molecular polarisability. The apparent conformations of thianthren and of three of its oxides as solutes in benzene". Journal of the Chemical Society (Resumed): 571–575. doi:10.1039/JR9650000571.
  5. ↑ US patent 3997560, "Process for the manufacture of thianthrene", issued 1976-12-14.
  6. ↑ Stenhouse, J. (1869). "Ueber die Producte der trockenen Destillation der sulfobenzolsauren Salze". Annalen der Chemie und Pharmacie 149 (2): 247–255. doi:10.1002/jlac.18691490216.
  7. ↑ W. Dilthey: Versammlungsberichte Bonner Chemische Gesellschaft, Angewandte Chemie, Volume 42, Issue 24, pp. 668–670, 15. June 1929; doi:10.1002/ange.19290422405.
  8. ↑ Shine, Henry J. (July 1998). "EPR and the History of the Thianthrene Cation Radical". Foundations of modern EPR. ISBN 978-981-02-3295-5.