Effect of Intramolecular Hydrogen Bonds on the Binding Efficiency of Compounds Containing Aminoalcohol‐Based Subunits in Combination with Heterocyclic Groups

Aminoalcohols represent an important class of compounds and serve as building blocks for numerous biologically active molecules, pharmaceutically relevant substances, chiral ligands, and other functional systems. In this study, these building blocks were incorporated into acyclic receptor architectures by modifying the structure of previously developed high‐affinity carbohydrate receptors. These modifications included the incorporation of hydroxy groups in such a way that, together with the already existing aliphatic amino groups, they form substructures based on 2‐aminoethanol or 3‐aminopropanol. The aim of this study was to investigate the extent to which the binding effectiveness is influenced by the presence of these substructures, which tend to form intramolecular hydrogen bonds between the hydroxy and amino groups. Binding studies, involving 1 H NMR spectroscopic titrations, solid–liquid extractions, and segment fusion chip calorimetry, revealed that the structural variations implemented had a significant impact on the binding effectiveness of the compounds under investigation. This study broadens our understanding of the role of intramolecular interactions in molecular recognition and highlights the importance of considering their formation when designing artificial receptors, new drugs, and related systems.