Carboxymethylated cyclodextrins and their complexes with Pr(III) and Yb(III) as water-soluble chiral NMR solvating agents for cationic compounds.

Abstract:

:Cyclodextrins that are indiscriminately carboxymethylated at the 2-, 3-, and 6-positions are used as chiral NMR solvating agents for cationic substrates with phenyl, naphthyl, pyridyl, indoline, and indole rings. Enantiodifferentiation with the alpha-, beta-, and gamma-cyclodextrin derivatives is compared. The carboxymethylated derivatives are almost always more effective as chiral NMR solvating agents for cationic substrates than native cyclodextrins. The most effective carboxymethylated cyclodextrin varies for different substrates, and at times even different resonances of the substrate. Addition of paramagnetic praseodymium(III) or ytterbium(III) to mixtures of the carboxymethylated cyclodextrin and substrate often causes enhancements in enantiomeric discrimination and facilitates measurements of enantiomeric purity. The lanthanide ion bonds to the carboxymethyl groups and causes perturbations in the chemical shifts in the NMR spectra of substrate molecules in the cyclodextrin cavity.

journal_name

Chirality

journal_title

Chirality

authors

Provencher KA,Weber MA,Randall LA,Cunningham PR,Dignam CF,Wenzel TJ

doi

10.1002/chir.20748

subject

Has Abstract

pub_date

2010-03-01 00:00:00

pages

336-46

issue

3

eissn

0899-0042

issn

1520-636X

journal_volume

22

pub_type

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