Sulfamide

Sulfamide[1]
Names
	IUPAC name Sulfuric diamide
	Other names Sulphamide; Sulfuryl amide
Identifiers
CAS Number	7803-58-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29368 ;
ChEMBL	ChEMBL355001 ;
ChemSpider	74243 ;
ECHA InfoCard	100.029.330
PubChem CID	82267;
UNII	VS7TZW634V ;
CompTox Dashboard (EPA)	DTXSID5064885 ;
	InChI InChI=1S/H4N2O2S/c1-5(2,3)4/h(H4,1,2,3,4) Key: NVBFHJWHLNUMCV-UHFFFAOYSA-N ; 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).
	verify (what is ?)
	Infobox references

Sulfamide (IUPAC name: sulfuric diamide) is a chemical compound with the molecular structure H₂NSO₂NH₂. 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 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, and iodine. Sulfur dioxide is believed to be activated through a series of intermediates: Et₃N-I⁺-I⁻, Et₃N-I⁺-I₃⁻ and Et₃N⁺-SO₂⁻.

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

gollark: What exactly is your goal with "creating a class"?

gollark: ↑

gollark: Absolute ones I think.

gollark: Laptop maybe?

gollark: So 0, which is probably considered false.

References

Merck Index, 11th Edition, 8894.
Regnault, Victor (1838) "Sur l'acide chlorosulfurique et la sulfamide" (On sulfuryl chloride and sulfamide), Annales de chimie et de physique, series 2, 69 : 170-184; see especially "Action de gaz ammoniac sec sur la liqueur chlorosulfurique" (Action of dry ammonia gas on liquid sulfuryl chloride), pages 176-180.
Leontiev, A. V.; Dias, H. V. R.; Rudkevich, D. M. (2006). "Sulfamides and sulfamide polymers directly from sulfur dioxide". Chemical Communications. 2006 (27): 2887–2889. doi:10.1039/b605063h.
Reitz‌, A. B.; Smith‌, G. R.; Parker‌, M. H. (2009). "The Role of Sulfamide Derivatives in Medicinal Chemistry: A Patent Review (2006 – 2008)". Expert Opinion on Therapeutic Patents. 19 (10): 1449–1453. doi:10.1517/13543770903185920. PMID 19650745.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Merck Index, 11th Edition, 8894.

[2] Regnault, Victor (1838) "Sur l'acide chlorosulfurique et la sulfamide" (On sulfuryl chloride and sulfamide), Annales de chimie et de physique, series 2, 69 : 170-184; see especially "Action de gaz ammoniac sec sur la liqueur chlorosulfurique" (Action of dry ammonia gas on liquid sulfuryl chloride), pages 176-180.

[3] Leontiev, A. V.; Dias, H. V. R.; Rudkevich, D. M. (2006). "Sulfamides and sulfamide polymers directly from sulfur dioxide". Chemical Communications. 2006 (27): 2887–2889. doi:10.1039/b605063h.

[4] Reitz‌, A. B.; Smith‌, G. R.; Parker‌, M. H. (2009). "The Role of Sulfamide Derivatives in Medicinal Chemistry: A Patent Review (2006 – 2008)". Expert Opinion on Therapeutic Patents. 19 (10): 1449–1453. doi:10.1517/13543770903185920. PMID 19650745.

Sulfamide

Sulfamide functional group

See also

References