Abstract
For investigating the mechanism of chiral recognition by cellulose derivatives, 13C NMR spectra of 1-phenylethanol were measured in CDCl3 in the presence or absence of cellulose tris(4-methylbenzoate) (1). (R)- and (S)-enantiomers of 1-phenylethanol showed different chemical shifts in the presence of 1. The degree of chemical shift difference was large at aromatic ipso carbon (1′-C) and methine carbon (1-C) with a hydroxyl group. Spin-lattice relaxation times (T1s) were also measured to compare mobilities of the enantiomers. In the presence of 1, T1 for each carbon of the (R)-enantiomer was shorter than that for corresponding carbon of the (S)-enantiomer. The presence of 1 restricts the mobility of the (R)-enantiomer more than that of the (S)-enantiomer. T1 difference between (R)- and (S)-enantiomers was large at 1-C. The results indicate that 1-phenylethanol is chirally recognized by 1 at the point of 1-C carbon.
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Oguni, K., Matsumoto, A. & Isokawa, A. 13C NMR Study on Diastereomeric Interactions between Cellulose Tris(4-methylbenzoate) and 1-Phenylethanol Enantiomers. Polym J 26, 1257–1261 (1994). https://doi.org/10.1295/polymj.26.1257
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DOI: https://doi.org/10.1295/polymj.26.1257