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Enantiodifferentiation of α-hydroxyalkanephosphonic acids in 31P NMR with application of α-cyclodextrin as chiral discriminating agent

✍ Scribed by Ewa Rudzińska; Gabriela Dziȩdzioła; Łukasz Berlicki; Paweł Kafarski

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
181 KB
Volume
22
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

α‐Cyclodextrin was shown to be convenient chemical shift reagent for determination of the enantiomeric composition of α‐hydroxyphosphonic acids by means of ^31^P NMR. The developed methodology appeared to be reliable, repetitive, easy to perform and simple for interpretation. Enantiomeric discrimination in the ^31^P NMR spectra for 12 of 13 studied hydroxyphosphonates was achieved, with baseline separation of resonances obtained for eight compounds. In those cases, the chemical nonequivalence values ranged from 0.069 to 0.313 ppm. The studies showed that enantioselectivity is strongly influenced by the solution pD and the optimal condition was found at pD 2 or 10 depending on the guest structure. On the basis of the ROESY spectra the complexation modes of selected hydroxyphosphonates with α‐cyclodextrin was postulated. Chirality 2010. © 2009 Wiley‐Liss, Inc.

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