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A versatile ternary ionic complex for chiral discrimination of molecules with diverse functionalities using H-1 NMR

Pal, Indrani and Chaudhari, Sachin Rama and Suryaprakash, Nagarajarao (2014) A versatile ternary ionic complex for chiral discrimination of molecules with diverse functionalities using H-1 NMR. In: NEW JOURNAL OF CHEMISTRY, 38 (10). pp. 4908-4912.

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Official URL: http://dx.doi.org/10.1039/c4nj00417e

Abstract

This study reports a simple, efficient and versatile protocol developed for NMR spectroscopic enantiodiscrimination of molecules containing diverse functional -groups, such as amino alcohols, secondary alcohols, cyanohydrins, oxazolidones, diols, thiones and epoxides, using a phosphorous based three component mixture. The simple mixing and shaking of enantiopure 1,1'-binaphthyt-2,2'-diyl hydrogenphosphate (BNPA), 4-(dimethylamino)pyridine (DMAP) and a chiral analyte in the solvent CDCl3 served as a chiral solvating agent and resulted in well dispersed peaks for each enantiomer in the H-1 NMR spectrum. Discrimination could be achieved not only for the proton at the chiral centre, but also for multiple proton sites. The devised approach also permitted the precise measurement of the enantiomeric excess (ee).

Item Type: Journal Article
Additional Information: Copyright for this article belongs to the ROYAL SOC CHEMISTRY, THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND.
Department/Centre: Division of Chemical Sciences > NMR Research Centre (Formerly Sophisticated Instruments Facility)
Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Depositing User: Id for Latest eprints
Date Deposited: 08 Nov 2014 05:28
Last Modified: 08 Nov 2014 05:28
URI: http://eprints.iisc.ac.in/id/eprint/50198

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