Hydrogen bonding chiral recognition

The chiral recognition mechanism for these types of phases was attributed primarily to hydrogen bonding and dipole—dipole interactions between the analyte and the chiral selector in the stationary phase. It was postulated that chiral recognition involved the formation of transient five- and seven-membered association complexes between the analyte and the chiral selector (117). 

Molecular recognition, 16 768-811 24 31 at the air-water interface, 16 799-800 artificial receptors for substrate recognition, 16 792-794 charge attraction dominated, 16 779-781 chiral recognition, 16 789-791 hydrogen bond dominated, 16 781-782 at interfaces and surface monolayers, 16 796-801... 

Affinity liquid chromatography and chiral separations (enantiomer separations) require similar analyte properties. The solutes may have interactions through hydrogen-bonding, ligand formation, or Coulombic forces with the surface of stationary phase materials or the sites of additives however, the selectivity is controlled by the steric effects of the structures of the analyte molecules and the recognition molecules (chiral selectors). 

Noncovalent interactions play a key role in biodisciplines. A celebrated example is the secondary structure of proteins. The 20 natural amino acids are each characterized by different structures with more or less acidic or basic, hydrophilic or hydrophobic functionalities and thus capable of different intermolecular interactions. Due to the formation of hydrogen bonds between nearby C=0 and N-H groups, protein polypeptide backbones can be twisted into a-helixes, even in the gas phase in the absence of any solvent." A protein function is determined more directly by its three-dimensional structure and dynamics than by its sequence of amino acids. Three-dimensional structures are strongly influenced by weak non-covalent interactions between side functionalities, but the central importance of these weak interactions is by no means limited to structural effects. Life relies on biological specificity, which arises from the fact that individual biomolecules communicate through non-covalent interactions." " Molecular and chiral recognition rely on... 

---