Distorted Fivefold-Diamond Structure of 4,4-Bis(2-carboxyethyl)pimelic Acid (‘Methanetetrapropionic Acid’)

✍ Scribed by Otto Ermer; Andreas Kusch; Christof Röbke

• Book ID: 102254219
• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 234 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390110

✦ Synopsis

Abstract

The molecules of 4,4‐bis(2‐carboxyethyl)pimelic acid (=4,4‐bis(2‐carboxyethyl)heptanedioic acid; 1) assemble to build up hollow, five‐fold interpenetrating diamond‐like networks in tetragonal crystals via standard pairwise H‐bonds between the carboxy groups. In keeping with the flat, extended molecular conformation of 1 of approximate D~2d~ symmetry, the supramolecular diamondoid networks are tetragonally compressed. Their mode of interpenetration is unusual and corresponds to that of adamantane‐1,3,5,7‐tetracarboxylic acid, which has an undistorted five‐fold diamond structure. Both the degree and the mode of interpenetration of 1 differ from those of the lower homologue 3,3‐bis(carboxymethyl)glutaric acid (2), which adopts a more‐common tetragonally elongated triple‐diamond architecture in the solid state.