Attempted covalent imitation of a supramolecular synthon moiety embedded in a crystalline hydrogen-bonded aggregate structure

Abstract

Imitative of a supramolecular synthon moiety D comprising two 3,5-bis(hydroxymethyl) substituted benzoic acid moieties (2), the covalently linked surrogate molecule 1 has been designated and synthesized. Crystal structures have been compared including also substituted and molecularly elongated derivatives of 2. They show largely common structural features in planar geometry of the building units and layer formation in the crystal packing, while the hydrogen bonded patterns within the layers differ according to the structural molecular changes. Moreover, synthon robustness of the dimer carboxylic acid motif has been confirmed.