Thianthrene is a sulfur-containing

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

. 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 Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...

analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...

dibenzodioxin Dibenzo-1,4-dioxin, also dibenzodioxin or dibenzo-''p''-dioxin (dibenzo-''para''-dioxin), is a polycyclic heterocyclic organic compound in which two benzene rings are connected by a 1,4-dioxin ring. Its molecular formula is C12H8O2. The two oxy ...

, the shape of thianthrene is not planar. It is bent, with a fold angle of 128° between the two benzo groups. Thianthrene can be prepared by treating

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

with

disulfur dichloride Disulfur dichloride (or disulphur dichloride by the British English spelling) is the inorganic compound of sulfur and chlorine with the Chemical formula, formula . It is an amber oily liquid. Sometimes, this compound is incorrectly named ''sulfur ...

in the presence of

aluminium chloride Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms a hexahydrate with the formula , containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are col ...

History

Thianthrene was first synthesized by

John Stenhouse John Stenhouse FRS FRSE FIC FCS (21 October 1809 – 31 December 1880) was a British chemist. In 1854, he invented one of the first practical respirators. He was a co-founder of the Chemical Society in 1841. Life John Stenhouse was born i ...

by dry distillation of

sodium benzenesulfonate Sodium benzenesulfonate is an organic compound with the formula . It is white, water-soluble solid, It is produced by the neutralization benzenesulfonic acid with sodium hydroxide. It is also a common ingredient in some detergents. The compou ...

. Thianthrene is oxidized by

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

forming a red radical cation. Thianthrene^•+ has been characterized by

Electron paramagnetic resonance Electron paramagnetic resonance (EPR) or electron spin resonance (ESR) spectroscopy is a method for studying materials that have unpaired electrons. The basic concepts of EPR are analogous to those of nuclear magnetic resonance (NMR), but the spin ...

. Four different publications describe the crystal structure of salts of thianthrene^•+.

References

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