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In organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...
, a thial or thioaldehyde is a functional group
In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
which is similar to an aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
, , in which a sulfur
Sulfur ( American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms ...
(S) atom replaces the oxygen
Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...
(O) atom of the aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
(R represents an alkyl
In organic chemistry, an alkyl group is an alkane missing one hydrogen.
The term ''alkyl'' is intentionally unspecific to include many possible substitutions.
An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...
or aryl
In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used ...
group). Thioaldehydes are even more reactive than thioketone
In organic chemistry, thioketones (; also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of , thioketones have the structure ...
s. Unhindered thioaldehydes are generally too reactive to be isolated — for example, thioformaldehyde
Thioformaldehyde is the organosulfur compound with the formula CH2S. It is the simplest thioaldehyde. This compound is not observed in the condensed state (solid or liquid) because it oligomerizes to 1,3,5-trithiane, which is a stable colorless ...
, , condenses to the cyclic trimer 1,3,5-trithiane
1,3,5-Trithiane is the chemical compound with the formula (CHS). This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether grou ...
. Thioacrolein, , formed by decomposition of allicin
Allicin is an organosulfur compound obtained from garlic and leeks. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin is unstable and quickl ...
from garlic
Garlic (''Allium sativum'') is a species of bulbous flowering plants in the genus '' Allium''. Its close relatives include the onion, shallot, leek, chives, Welsh onion, and Chinese onion. Garlic is native to central and south Asia, str ...
, undergoes a self Diels-Alder reaction giving isomeric vinyldithiin
Vinyldithiins, more precisely named 3-vinyl-4''H''-1,2-dithiin and 2-vinyl-4''H''-1,3-dithiin, are organosulfur phytochemicals formed in the breakdown of allicin from crushed garlic (''Allium sativum''). Vinyldithiins are Diels-Alder dimers of thi ...
s. While thioformaldehyde is highly reactive, it is found in interstellar space along with its mono- and di-deuterated isotopologue
In chemistry, isotopologues (also spelled isotopologs) are molecules that differ only in their isotopic composition. They have the same chemical formula and bonding arrangement of atoms, but at least one atom has a different number of neutrons t ...
s. With sufficient steric bulk, however, stable thioaldehydes can be isolated.
In early work, the existence of thioaldehydes was inferred by trapping processes. For instance the reaction of with benzaldehyde
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful.
It is a colorless liquid with a characteristic almond-li ...
was proposed to form thiobenzaldehyde, which forms a cycloadduct with the dithiophosphine ylides to form a ring.
See also
*Thioketone
In organic chemistry, thioketones (; also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of , thioketones have the structure ...
*Thioenol
In organic chemistry, thioenols (also known as alkenethiols) are alkenes with a thiol group () affixed to one of the carbon atoms composing the double bond (i.e. ). They are the sulfur analogs of enols (hence the ''thio-'' prefix). Alkenes with a ...
*Organosulfur compounds
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
Further reading
* *References
{{Authority control Functional groups