Thianthrene is a sulfur-containing heterocyclic chemical compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

. It is the sulfur analog

Analog (chemistry)

In chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...

 of dibenzodioxin

Dibenzodioxin

Dibenzo-p-dioxin or dibenzo-1,4-dioxin is an organic heterocyclic compound in which two benzene rings are connected by a 1,4-dioxin ring. Its molecular formula is C12H8O2...

 (commonly known as dioxin). Unlike dioxins, the shape of thianthrene is not planar. It is bent, with an angle of 128° between the two benzene rings.

Thianthrene can be prepared by reacting disulfur dichloride

Disulfur dichloride

Disulfur dichloride is the chemical compound with the formula S2Cl2 . Some alternative names for this compound are sulfur monochloride , disulphur dichloride and sulphur monochloride...

 with benzene

Benzene

Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 in the presence of aluminium chloride

Aluminium chloride

Aluminium chloride is the main compound of aluminium and chlorine. It is white, but samples are often contaminated with iron trichloride, giving it a yellow colour. The solid has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium metal, but large...

.

History

Thianthrene was first synthesized by John Stenhouse

John Stenhouse

John Stenhouse FRS FRSE FIC FCS was a Scottish chemist. In 1854, he invented one of the first practical respirators.He was a co-founder of the Chemical Society in 1841.-Life:...

 by dry distillation of benzenesulfonic acid

Benzenesulfonic acid

Benzenesulfonic acid is an organosulfur compound with the formula C6H5SO3H. It is the simplest aromatic sulfonic acid. It forms colorless deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in carbon disulfide and diethyl...

 sodium salt. Thianthrene reacts with sulfuric acid

Sulfuric acid

Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...

 forming a red product. R. Wizinger was the first to publish the structure of the colour giving cationic radical in 1929. Although the structure was published several researchers used Thianthrene^•+ for Electron paramagnetic resonance

Electron paramagnetic resonance

Electron paramagnetic resonance or electron spin resonance spectroscopyis a technique for studying chemical species that have one or more unpaired electrons, such as organic and inorganic free radicals or inorganic complexes possessing a transition metal ion...

studies in the 1960s. Four different publications on the structure of Thianthrene^•+ were published without knowledge of the other research.