32fc41b8cf8ee838418a59d6abf02a75 mol_a2019v24n2p352.pdf 69394be3ff5ec7af0082f7c193c45a8a52f685c6 mol_a2019v24n2p352.pdf 69cc931715cc9c382950ad0d19853ad938f10b024a3c8c7060248a20d6eb8d29 mol_a2019v24n2p352.pdf Title: Synthesis and Gelling Abilities of Polyfunctional Cyclohexane-1,2-dicarboxylic Acid Bisamides: Influence of the Hydroxyl Groups Subject: New enantiomerically pure C16-alkyl diamides derived from trihydroxy cyclohexane-1, 2-dicarboxylic acid have been synthesized from (-)-shikimic acid. The hydroxyl groups in these compounds are free or, alternatively, they present full or partial protection. Their gelling abilities towards several solvents have been tested and rationalized by means of the combined use of Hansen solubility parameters, scanning electron microscopy (SEM), and circular dichroism (CD), as well as computational calculations. All the results allowed us to account for the capability of each type of organogelator to interact with different solvents and for the main mode of aggregation. Thus, compounds with fully protected hydroxyl groups are good organogelators for methanol and ethanol. In contrast, a related compound bearing three free hydroxyl groups is insoluble in water and polar solvents including alcohols but it is able to gelate some low-polarity solvents. This last behavior can be justified by strong hydrogen bonding between molecules of organogelator, which competes advantageously with polar solvent interactions. As an intermediate case, an organogelator with two free hydroxyl groups presents an ambivalent ability to gelate both apolar and polar solvents by means of two aggregation patterns. These involve hydrogen bonding interactions of the unprotected hydroxyl groups in apolar solvents and intermolecular interactions between amide groups in polar ones. Keywords: polyfunctional cycloalkane bisamides; organogelator; self-assembly; chirality; hydrogen bonds Author: Bernat Pi-Boleda, María Campos, Marta Sans, Antonio Basavilbaso, Ona Illa, Vicenç Branchadell, Juan Carlos Estévez and Rosa M. 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