Macrocyclic compound

Article By:

Gokel, George W. Department of Chemistry and Biochemistry, University of Missouri, St. Louis, Missouri.

Last reviewed:January 2020

DOI:https://doi.org/10.1036/1097-8542.169200

An organic compound that contains a large ring. In the organic chemistry of alicyclic compounds, a closed chain of 12 carbon (C) atoms is usually regarded as the minimum size for a large ring; crown ethers are similarly defined. Macrocyclic compounds may be a single, continuous thread of atoms, as in cyclododecane [(CH₂)₁₂], or they may incorporate more than one strand or other ring systems (subcyclic units) within the macrocycle or macroring. In addition, macrocycles may be composed of aromatic rings that confer considerable rigidity upon the cyclic system. These aromatic rings may be joined together or coupled by spacer units consisting of one or more carbon atoms. The compounds generally thought of as macrocycles include crown ethers, cryptands, spherands, carcerands, cyclodextrins, cyclophanes, calixarenes, resorcinarenes, pyrogallolarenes, and hybrids of all of them. See also: Aromatic hydrocarbon

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