Sulfinamide is a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...

in organosulfur chemistry with the structural formula RS(O)NR'₂ (where R and R' are organic substituents). This functionality is composed of a

sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formul ...

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes ...

(S–C) and sulfur-

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seve ...

(S–N) single bonds, as well as a sulfur-

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as we ...

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

(S=O), resulting in a tetravalent sulfur centre (in resonance with its

zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively- and negatively-charged functional groups. : With amino acids, for example, in solution a chemical equilibrium w ...

ic form). As a non-bonding electron pair is also present on the sulfur, these compounds are also chiral. They are sometimes referred to as ''S''-

chiral Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from i ...

sulfinamides. Sulfinamides are

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...

s of sulfinic acid (RS(O)OH). ZIJGUW

Structure

Sulfinamides do not undergo inversion. They can therefore be synthesised and/or isolated in enantiopure forms. This has led to their use as chiral

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogeno ...

equivalents and more broadly as

chiral auxiliaries In stereochemistry, a chiral auxiliary is a Stereogenic center, stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. The chirality present in the auxil ...

Synthesis

Sulfinamides are traditionally produced by the reaction of sulfinyl chlorides with primary or secondary amines. They also arise by the addition of Grignard reagents to

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 ...

s, followed by protonation: :RMgX + R'N=S=O → RS(O)(NR'MgX) :RS(O)(NR'MgX) + H₂O → RS(O)(NR'H) + "MgX(OH)" Yet another route entails peracid-oxidation of sulfenylphthalimides, which gives sulfinylphthalimides.

Examples

A common sulfinamide is ''tert''-butanesulfinamide (Ellman's sulfinamide), ''p''-toluenesulfinamide (Davis' sulfinamide), and 2,4,6-trimethylbenzenesulfinamide. Sulfinamides arise in nature by the addition of nitroxyl (HNO) to

thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...

s: :RSH + HNO → RS(O)NH₂

References

Amides Functional groups {{organic-chem-stub