Sulfoxide

Definition

A sulfoxide is a functional group in organic chemistry that consists of a sulfur atom double-bonded to an oxygen atom. Sulfoxides are important intermediates in various organic reactions and have diverse applications in chemistry and biology.

5 Must Know Facts For Your Next Test

1. Sulfoxides can be synthesized by the oxidation of sulfides, which involves the addition of an oxygen atom to the sulfur atom.
2. Sulfoxides are commonly used as chiral auxiliaries in asymmetric synthesis, as they can induce stereochemical control in certain reactions.
3. The sulfur-oxygen bond in sulfoxides is polar, with the sulfur atom bearing a partial positive charge and the oxygen atom bearing a partial negative charge.
4. Sulfoxides can undergo further oxidation to form sulfones, which have two oxygen atoms bonded to the sulfur atom.
5. Dimethyl sulfoxide (DMSO) is a widely used sulfoxide compound that has various applications in organic synthesis, biology, and medicine.

Review Questions

• Explain the relationship between sulfoxides and thiols in the context of 18.7 Thiols and Sulfides.
  • Sulfoxides are related to thiols (organic compounds containing a sulfhydryl group, -SH) in the sense that they can be formed by the oxidation of sulfides, which are the sulfur analogues of ethers. The oxidation of a sulfide to a sulfoxide involves the addition of an oxygen atom to the sulfur atom, resulting in a polar sulfur-oxygen bond. This transformation is an important step in the chemistry of thiols and sulfides, as sulfoxides can serve as intermediates in various organic reactions.
• Describe the role of sulfoxides in asymmetric synthesis, and how they can be used to induce stereochemical control.
  • Sulfoxides are commonly used as chiral auxiliaries in asymmetric synthesis, a technique that allows for the selective formation of one enantiomer of a chiral compound over the other. The presence of the sulfur-oxygen bond in sulfoxides creates a chiral center, and the specific stereochemistry of the sulfoxide can be used to control the stereochemistry of the products in certain reactions. This is achieved by the sulfoxide group interacting with other reactants in a stereospecific manner, guiding the formation of the desired enantiomer.
• Discuss the importance of dimethyl sulfoxide (DMSO) as a sulfoxide compound, and explain its diverse applications in organic synthesis, biology, and medicine.
  • Dimethyl sulfoxide (DMSO) is a widely used sulfoxide compound that has a wide range of applications. In organic synthesis, DMSO is a versatile solvent and reagent that can participate in various reactions, such as oxidations and substitutions. In biology, DMSO is used as a cryoprotectant to preserve cells and tissues during freezing, and it has also been studied for its potential therapeutic properties, including its ability to penetrate the skin and deliver drugs. In medicine, DMSO is used in the treatment of certain conditions, such as interstitial cystitis and some types of pain, due to its anti-inflammatory and analgesic properties. The unique properties of DMSO, including its polarity, high dielectric constant, and ability to penetrate biological membranes, make it a valuable compound in both research and practical applications.

Related terms

Thiol: A thiol is an organic compound that contains a sulfhydryl group (-SH), which is a sulfur-hydrogen bond. Thiols are the sulfur analogues of alcohols and are important in many biological processes.

Sulfide: A sulfide is a compound containing a sulfur atom bonded to one or more other elements, typically a metal or another sulfur atom. Sulfides are widely found in nature and have numerous applications in chemistry and industry.

Oxidation: Oxidation is a chemical reaction that involves the loss of electrons by a molecule, atom, or ion, resulting in an increase in its oxidation state. Oxidation is a key process in many chemical and biological reactions.