p-TsOH promotes 2′-amino-[1,1′-binaphthalene]-2-ol as a chiral solvating agent

Abstract

2′-Amino-[1,1′-binaphthalene]-2-ol (NOBIN) fails to serve as a chiral solvating agent (CSA) for acids, hydroxy acids and their derivatives due to its negligibly weak or absence of weak molecular interactions with the chiral analyte. In the present study, we demonstrate the utility of NOBIN as a CSA for discrimination of acids, hydroxy acids and their derivatives with a distinct strategy wherein a third ingredient, p-toluenesulphonic acid (p-TsOH), was introduced as a linker, which induces hydrogen bonding interactions and thus permits the NMR spectroscopic differentiation. The formation of ternary complex is further established by UV-Vis, fluorescence, IR and PXRD studies. Ternion complex structures were optimized by the DFT calculations.