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Sulfinylmethane or sulfine is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with molecular formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
H2CSO. It is the simplest sulfine. Sulfines are chemical compounds with the general structure XY=SO. IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
considers the term 'sulfine' obsolete, preferring instead thiocarbonyl ''S''-oxide, despite this the use of the term sulfine still predominates in the chemical literature.
Substituted sulfines
The parent sulfine H2CSO is very labile, whereas substituted derivatives are more conveniently isolated. One example issyn-propanethial-S-oxide
''syn''-Propanethial ''S''-oxide (or (''Z'')-propanethial ''S''-oxide), a member of a class of organosulfur compounds known as thiocarbonyl ''S''-oxides (formerly " sulfines"), is a volatile liquid that acts as a lachrymatory agent (triggers tear ...
which is produced from allicin
Allicin is an organosulfur compound obtained from garlic, a species in the family Alliaceae. It was first isolated and studied in the laboratory by Chester J. Cavallito and John Hays Bailey in 1944. When fresh garlic is chopped or crushed, the ...
and is responsible for eye-watering effects of cutting onions. Another example is diphenylsulfine, obtained by oxidation of thiobenzophenone
Thiobenzophenone is an organosulfur compound with the formula (C6H5)2CS. It is the prototypical thioketone. Unlike other thioketones that tend to dimerize to form rings and polymers, thiobenzophenone is quite stable, although it photoxidizes in ...
:
:(C6H5)2C=S + → (C6H5)2C=S=O
See also
*Sulfene
Sulfene is an extremely reactive chemical compound with the formula H2C=SO2. It is the simplest member of the sulfenes, the group of compounds which are ''S'',''S''-dioxides of thioaldehydes and thioketones, and have the general formula R2C=SO2.
...
- related functional group with the formula H2C=SO2
*Ethenone
In organic chemistry, ethenone is the formal name for ketene, an organic compound with formula or . It is the simplest member of the ketene class. It is an important reagent for acetylations.
Properties
Ethenone is a highly reactive gas (a ...
*Heterocumulene A heterocumulene is a molecule or ion containing a chain of at least three double bonds between consecutive atoms, in which one or more atoms in the doubly bonded chain is a heteroatom. Such species are analogous to a cumulene in which the chain of ...
References
Organosulfur compounds {{organic-compound-stub