Difference Between Sulfone and Sulfoxide

The key difference between sulfone and sulfoxide is that sulfone compound has two double-bonded oxygen atoms, whereas sulfoxide has only one double-bonded oxygen atom.

Sulfone and sulfoxide are organic compounds. Both these compounds contain central sulfur atoms that are bonded to oxygen atoms and alkyl or aryl organic groups. Sulfone is an organic compound containing a sulfonyl functional group attached to two carbon atoms while sulfoxides are organic compounds containing a central sulfur atom attached to two carbon atoms and an oxygen atom.

CONTENTS

1. Overview and Key Difference
2. What is Sulfone 
3. What is Sulfoxide
4. Similarities Between Sulfone and Sulfoxide
5. Side by Side Comparison – Sulfone vs Sulfoxide in Tabular Form
6. Summary

What is Sulfone?

Sulfone is an organic compound containing a sulfonyl functional group attached to two carbon atoms. Therefore, the sulfur atom is at the centre of the compound, and it shows hexavalency. This sulfur atom has two double-bonded oxygen atoms attached to it. The oxidation state of this sulfur atom is +6. Usually, the two carbon atoms attached to the central sulfur atom are in two separate hydrocarbon substituents.

There are some different methods to produce a sulfone compound. The most common method is the oxidation of thioesters and sulfoxides. E.g. oxidation of dimethyl sulfide forming dimethyl sulfoxide followed by the conversion into dimethyl sulfone. Further, we can produce sulfone compounds from SO2, which is a convenient and widely used source of sulfonyl functional group. In addition, we can produce sulfone from sulfonyl and sulfuryl halides as well.

There are different applications of sulfone. It is important to extract valuable aromatic compounds from petroleum, in the manufacture of polymer materials, in pharmacology, etc.

What is Sulfoxide?

Sulfoxides are organic compounds containing a central sulfur atom attached to two carbon atoms and an oxygen atom. It contains the sulfinyl functional group, which is a polar group (oxygen atom has a partial negative charge while sulfur atom has a particle positive charge). These compounds are the derivatives of sulfides which are formed from oxidation.

Typically, sulfoxides are formed from the oxidation of sulfides in the presence of oxidants such as hydrogen peroxide. However, we need to carefully handle these oxidation reaction mixtures because these can be aggressive reactions. In addition, we can produce sulfoxides from sulfur dioxide through a Friedel-Craft arylation reaction.

There are some important applications of sulfoxides – using as a solvent, used in the production of some drugs such as esomeprazole, as catalysts, etc.

What are the Similarities Between Sulfone and Sulfoxide?

• Sulfone and sulfoxide are organic compounds.
• These compounds contain central sulfur atoms.
• Both these compounds contain S=O bonds.

What is the Difference Between Sulfone and Sulfoxide?

Sulfone and sulfoxide are organic compounds containing sulfur atoms. Sulfone is an organic compound containing a sulfonyl functional group attached to two carbon atoms while sulfoxides are organic compounds containing a central sulfur atom attached to two carbon atoms and an oxygen atom. The key difference between sulfone and sulfoxide is that sulfone compound has two double-bonded oxygen atoms, whereas sulfoxide has only one double-bonded oxygen atom.

The following infographic summarizes the differences between sulfone and sulfoxide in tabular form for side by side comparison.

Summary – Sulfone vs Sulfoxide

Sulfone is an organic compound containing a sulfonyl functional group attached to two carbon atoms. Sulfoxides are organic compounds containing a central sulfur atom attached to two carbon atoms and an oxygen atom. The key difference between sulfone and sulfoxide is that sulfone compound has two double-bonded oxygen atoms whereas sulfoxide has only one double-bonded oxygen atom.

Reference:

1. “Sulfoxide.” Sulfoxide – ScienceDirect Topics, Available here.

Image Courtesy:

1. “Sulfone” By Sulfone.png: Benjah-bmm27derivative work: Vladsinger (talk) – Sulfone.png (Public Domain) via Commons Wikimedia
2. “Sulfoxide-tetrahedral” By Nothingserious – Own work (Public Domain) via Commons Wikimedia