Synthesis and X-ray Structure of Amide-Based Macrocycles, Catenanes and Pretzelane

Abstract

The syntheses and crystal structure studies of amide-based catenanes derived from m-phenylene diacrylic acid and 5-acetoxy isophthalic acid (17% and 3% yield of 4a and 4b resp.) and octalactam macrocycles (21% yield of 3) are described. Hydrogen bonding patterns play a key role in the formation of the different conformations of octalactam 3. The crystal structures of 3 reveal a number of hydrogen-bonding interactions between the macrocycle and two different solvent molecules, which are presumably responsible for the different conformations. Furthermore, we report the X-ray structure of a catenane, which was converted into a “pretzelane” by bridging two phenolic hydroxy groups with a p-xylylene unit.