''N''-Sulfinylaniline is the

organosulfur compound Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...

with the formula . It is a straw-colored liquid. ''N''-Sulfinylaniline is an example of a

sulfinylamine 153 px, ''N''-Sulfinylaniline is a common sulfinylamine Sulfinylamines (formerly ''N''-sulfinyl amines) are organosulfur compounds with the formula RNSO where R = an organic substituent. These compounds are, formally speaking, derivatives of HN ...

. It is a dienophile and a

ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...

organometallic chemistry Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...

Synthesis and structure

It is prepared by treating

aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...

with

thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately Volatility (chemistry), volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a Halogenation, chlorinating reagen ...

: : X-ray crystallographic analysis confirms that ''N''-sulfinylaniline is structurally related to sulfur dioxide as well as

sulfur diimide Sulfur diimides are chemical compounds of the formula S(NR)2. Structurally, they are the diimine of sulfur dioxide. The parent member, S(NH)2, is of only theoretical interest. Other derivatives where R is an organic group are stable and useful rea ...

. The C–S=N=O dihedral angle is –1.60°.

References

{{DEFAULTSORT:Sulfinylaniline, N- Sulfur(IV) compounds Phenyl compounds