''N''-Sulfinylaniline is the

organosulfur compound Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfu ...

with the formula C₆H₅NSO. 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 H ...

. It is a dienophile and a

ligand In coordination chemistry, a ligand is an ion or molecule (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 electr ...

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 is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...

with thionyl chloride: :3 PhNH₂ + SOCl₂ → PhNSO + 2 hNH₃l 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