Sulfamide

Sulfamide (IUPAC name: sulfuric diamide) is a compound with the chemical formula SO₂(NH₂)₂ and structure H₂N−S(=O)₂−NH₂. Sulfamide is produced by the reaction of sulfuryl chloride with ammonia. Sulfamide was first prepared in 1838 by the French chemist Henri Victor Regnault.^[2]

Sulfamide^[1]

Names
IUPAC name Sulfuric diamide
Preferred IUPAC name Sulfamide
Other names Sulphamide Sulfuryl amide
Identifiers
CAS Number	7803-58-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29368 Y
ChEMBL	ChEMBL355001 Y
ChemSpider	74243 Y
ECHA InfoCard	100.029.330
PubChem CID	82267
UNII	VS7TZW634V Y
CompTox Dashboard (EPA)	DTXSID5064885
InChI InChI=1S/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4) Y Key: NVBFHJWHLNUMCV-UHFFFAOYSA-N Y InChI=1/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4) Key: NVBFHJWHLNUMCV-UHFFFAOYAV
SMILES O=S(=O)(N)N
Properties
Chemical formula	H4N2O2S
Molar mass	96.11 g/mol
Appearance	White orthorhombic plates
Melting point	93 °C (199 °F; 366 K)
Boiling point	250 °C (482 °F; 523 K) (decomposes)
Solubility in water	Freely soluble
Magnetic susceptibility (χ)	−44.4×10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Sulfamide functional group

In organic chemistry, the term sulfamide may also refer to the functional group which consists of at least one organic group attached to a nitrogen atom of sulfamide.

Symmetric sulfamides can be prepared directly from amines, sulfur dioxide gas and an oxidant:^[3]

In this example, the reactants are aniline, triethylamine (Et₃N, Et = ethyl group), and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et₃N−⁺−I⁻, Et₃N−I⁺−I−3 and Et₃N⁺−SO−2.

The sulfamide functional group is an increasingly common structural feature used in medicinal chemistry.^[4]

See also

• Sulfamic acid
• Sulfonamide