Determination of Enantiomeric Purity for Chiral π-Basic Aromatic Alcohols Chiral Samples by ¹H NMR Spectroscopy

N-3,5-Dinitrobenzoyl(DNB)-(R)-phenylglycinol (Sel 1) and its silylation product (Sel 2) were used as the HPLC chiral stationary phase (CSP) for the resolution of racemic analytes. 2,2,2-Trifluoro-1-(9-anthryl)ethanol (S1), 1,1′-bi-2-naphthol (S2), and 6,6′-dibromo-1,1′-bi-2-naphthol (S3) were separated on the CSP, but the enantiomeric purities could not be accurately determined because of low resolution (Rs). In this study, the enantiomeric purity of S1-S3 were determined using Sel 1, Sel 2, and 1,3-bis[(S)-methylbutoxy] calix[4]arene-2,4-diol (Sel 3). These were used for ¹H NMR experiments in three different solvents (CDCl₃, DMSO‑d₆, and acetone‑d₆). The accuracy of the enantiomeric purity of S1-S3 with Sel 2 was more than 98% when using CDCl₃.