P. Chaudhary, G. Yadav, Surendra Singh
Sep 5, 2022
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Journal
RSC Advances
Abstract
A rapid and simple protocol for the determination of enantiopurity of primary and secondary amines was developed by using (S)-BINOL/(S)-BINOL derivatives/(R)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate as chiral solvating agents via1H- and 19F-NMR spectroscopic analysis. In this protocol, the analyte and chiral solvating agent were directly mixed in an NMR tube in chloroform-d and after shaking for 30 seconds the 1H- and 19F-NMR spectra were recorded, which affords well-resolved resonance peaks for both the enantiomers present in an analyte. The enantiomeric excess of 1,2-diphenylethylenediamine was determined and linear relationship with coefficient of R2 = 0.9995 was observed. The binding constant and associated ΔG values were also calculated for diastereomeric complexes formed between both the enantiomers of analyte 5 with CSA (S)-3a by using UV-visible spectroscopy.