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Determination of Enantiomeric Purity for Chiral π‐Basic Aromatic Alcohols Chiral Samples by 1 H NMR Spectroscopy
Author(s) -
Heo Kyu Sung,
Ryoo Jae Jeong
Publication year - 2020
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11906
Subject(s) - chemistry , enantiomer , acetone , chiral derivatizing agent , resolution (logic) , silylation , proton nmr , enantiomeric excess , high performance liquid chromatography , chromatography , nuclear magnetic resonance spectroscopy , diol , chiral column chromatography , organic chemistry , medicinal chemistry , enantioselective synthesis , catalysis , artificial intelligence , computer science
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 1 H NMR experiments in three different solvents (CDCl 3 , DMSO‑ d 6 , and acetone‑ d 6 ). The accuracy of the enantiomeric purity of S1‐S3 with Sel 2 was more than 98% when using CDCl 3 .