sulfamates

Sulfamates are derivatives of sulfamic acid (H2NSO3H). They contain the sulfamoyl group (-SO2NH2) and include sulfamate esters (R–O–SO2–NH2) and sulfamate salts obtained when the acidic NH is neutralized or substituted. The group is common in organosulfur chemistry and may be further substituted on nitrogen or sulfur.

Sulfamate esters have general formula RO–SO2–NH2; substitution of the amide hydrogen by alkyl or aryl groups yields N-substituted sulfamates. The corresponding salts are formed by deprotonation of sulfamic acid and association with a metal or organic counterion.

Preparation of sulfamates can proceed via several routes. They are often prepared by reaction of alcohols with sulfamic acid under dehydrating conditions to give sulfamate esters. They can also form by neutralization of sulfamic acid with metal bases to give sulfamate salts, or by sulfonylation routes using chlorosulfonyl reagents.

Applications of sulfamates span organic synthesis and coordination chemistry. They serve as intermediates in the preparation of sulfonamides and heterocycles, and sulfamate esters are used as protecting groups for amines in multistep syntheses. Sulfamate ligands participate in various metal-complex formations, and several derivatives have been explored as enzyme inhibitors or bioactive intermediates in medicinal chemistry.

Safety considerations for sulfamates reflect their sulfur- and nitrogen-containing nature; they are generally handled with standard laboratory precautions, as they can be irritants and reactive under certain conditions.