Ipso, Meso, and Peri Substitutions in Organic Chemistry

Ring Substitutions of Organic Molecules

This shows the difference between ipso-, meso- and peri- arene substitution patterns.
This shows the difference between ipso-, meso- and peri- arene substitution patterns. Todd Helmenstine

 The prefixes ipso-, meso-, and peri- describe ring substitutions in organic chemistry. They are part of the IUPAC nomenclature used to specify the position of any non-hydrogen substituents in an aromatic hydrocarbon.

Ipso Substitution

The ipso- prefix is used when two substituents share the same ring position in an intermediate compound. This could occur in an electrophilic aromatic ring substitution.

Meso Substitution

The meso- prefix is used when substituents occupy a benzylic position, when the first carbon covalently bonds adjacent to a benzene or other aromatic ring. It is seen in acridines and calixarenes.

Peri Substitution

The peri- prefix is used to describe substituents at the 1 and 8 positions. It is seen specifically in naphthalenes.

In addition to ipso, meta, and peri, there are two other ring substitution patterns you may encounter. There is the ortho, meta, and para substitution and the cine and tele substitution.

Cine and Tele Substitution

In the cine- substitution, the entering group is positioned adjacent to the one that was occupied by the leaving group. This is seen in aryne chemistry.

In the tele- substitution, the new position of the entering group is more than one atom further away on the aromatic ring.

Format
mla apa chicago
Your Citation
Helmenstine, Anne Marie, Ph.D. "Ipso, Meso, and Peri Substitutions in Organic Chemistry." ThoughtCo, Feb. 28, 2017, thoughtco.com/ipso-meso-and-peri-substitutions-608695. Helmenstine, Anne Marie, Ph.D. (2017, February 28). Ipso, Meso, and Peri Substitutions in Organic Chemistry. Retrieved from https://www.thoughtco.com/ipso-meso-and-peri-substitutions-608695 Helmenstine, Anne Marie, Ph.D. "Ipso, Meso, and Peri Substitutions in Organic Chemistry." ThoughtCo. https://www.thoughtco.com/ipso-meso-and-peri-substitutions-608695 (accessed November 21, 2017).