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Preparation of a new chiral acridino-18-crown-6 ether-based stationary phase for enantioseparation of racemic protonated primary aralkyl amines |
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| Authors: | Szilvia Lakatos Ferenc Bertha Tünde Tóth György Orosz |
| Institution: | a Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, PO Box 91, Hungary b Research Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, H-1521 Budapest, PO Box 91, Hungary c Protein Modelling Group of the Hungarian Academy of Sciences, Eötvös Loránd University, H-1518 Budapest, 112, PO Box 32, Hungary d Reanal Fine Chemicals Co., H-1147 Budapest, Telepes u. 53, Hungary e Institute of Chemistry, Eötvös Loránd University, H-1518 Budapest, 112, PO Box 32, Hungary |
| Abstract: | Starting from commercially available and relatively cheap chemicals first enantiopure dimethyl-substituted monoaza-18-crown-6 ether (R,R)-21 containing a diphenylamine unit was prepared, which was then transformed to dimethyl-substituted acridino-18-crown-6 ligand (R,R)-19 having an N-allyl-carbamoyl linker by several steps. The terminal double bond of the latter made possible to attach (R,R)-19 to γ-mercaptopropyl-functionalized spherical HPLC quality silica gel obtaining a new chiral stationary phase (R,R)-CSP-37. Based on electronic circular dichroism (ECD) studies the N-allyl-carbamoyl group attached to the acridine ring of the chiral host (R,R)-19 does weaken exciton interaction between the host and guest molecules, but does not destroy the discriminating power of the chiral host. An HPLC column filled with (R,R)-CSP-37 was tested for the enantioseparation of racemic 1-(1-naphthyl)- and 1-(2-naphthyl)ethylamine hydrogenperchlorates using isocratic conditions. |
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