Organosulfur chemistry
Study of organic compounds containing sulfur.
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. These compounds are often associated with foul odors, but many of the sweetest compounds known, such as saccharin, are organosulfur derivatives. Nature abounds with organosulfur compounds, as sulfur is vital for life; of the 20 common amino acids, two (cysteine and methionine) are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels derived from ancient organisms necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.
- field
- Organic chemistry
- known_for
- Study of organosulfur compounds, including sulfides, thiols, disulfides, thioesters, and sulfoxides
Lore & Background
Organosulfur compounds can be classified according to sulfur-containing functional groups. Sulfides, formerly known as thioethers, are characterized by C−S−C bonds, which are longer and about 10% weaker than C−C bonds. Thiols are structurally similar to alcohols but are more nucleophilic, more acidic, and more readily oxidized. Disulfides with a covalent sulfur-to-sulfur bond are important for crosslinking in biochemistry and polymer chemistry. Thioesters are related to regular esters but are more susceptible to hydrolysis, and thioesters formed from coenzyme A are prominent in fatty acid synthesis.
Reader's Guide
Organosulfur chemistry is significant because sulfur is vital for life and appears in essential biomolecules such as the amino acids cysteine and methionine, as well as in antibiotics like penicillin and sulfa drugs. The field also encompasses compounds with industrial and environmental importance, such as organosulfur compounds in fossil fuels, whose removal is a major focus of oil refineries. The chemistry includes a wide range of functional groups, from sulfides and thiols to sulfoxides and sulfonic acids, with applications in pharmacology, agriculture, and materials science. The presence of sulfur in both beneficial and harmful compounds, such as sulfur mustard, highlights the dual nature of these substances.
Did You Know?
- Saccharin, one of the sweetest compounds known, is an organosulfur derivative.
- Thioesters formed from coenzyme A are prominent in fatty acid synthesis.
- Allicin is an example of a thiosulfinate, the S-oxide of a disulfide.
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