Abstract
We investigated the influence of various factors (including solvent mixtures) on chiral recognition of chiral carboxylates, using the titration method under 1H NMR control. We found that strong binding carboxylates (geometrical matching) is not enough for the satisfactory differentiation of enantiomers. Moreover, solvent mixture studies indicate a significant influence of environment on the formation of diastereomeric complexes and variations among them. Our findings offer insights into the complementarity of chiral recognition processes.
Highlights
Solving the puzzle of how nature works remains as an unending source of challenges for researchers.[1]
Chiral recognition phenomena originate from differences in the Gibbs free energy (ΔGtotal) of diastereomeric complexes formed between chiral molecules.[8]
ΔGtotal depends on the energy of intermolecular interactions (Einter), the energy from conformational changes (ΔEintra), and free solvation energy (ΔGsolv)
Summary
Solving the puzzle of how nature works remains as an unending source of challenges for researchers.[1]. Chiral recognition phenomena originate from differences in the Gibbs free energy (ΔGtotal) of diastereomeric complexes formed between chiral molecules.[8] ΔGtotal depends on the energy of intermolecular interactions (Einter), the energy from conformational changes (ΔEintra), and free solvation energy (ΔGsolv). Effective chiral recognition of anions requires the synthesis and determination of binding affinities and enantioselectivities of prospective chiral receptors.[15] Based on these considerations, we designed a series of chiral receptors (1a−1e) of various sizes and binding pocket geometries, with different arrangements of hydrogen bonding donors (Figure 2). We designed a series of chiral receptors (1a−1e) of various sizes and binding pocket geometries, with different arrangements of hydrogen bonding donors (Figure 2) To achieve this goal, we took the approach of using the covalent attachment of the chiral moiety to an anion binding backbone. We chose a peracetylated glucosamine derivative,[17] which is a cheap and readily available source of chirality and can be functionalized by changing the protecting groups
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