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NMR Enantiodiscrimination of Polar and Apolar Substrates by Multifunctional Cyclodextrins
Author(s) -
UccelloBarretta Gloria,
Balzano Federica,
Sicoli Giuseppe,
Scarselli Alessandro,
Salvadori Piero
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500506
Subject(s) - chemistry , enantiomer , polar , cyclodextrin , nuclear magnetic resonance spectroscopy , ring (chemistry) , organic chemistry , combinatorial chemistry , stereochemistry , computational chemistry , physics , astronomy
Mixed methylated/carbamoylated cyclodextrins constitute a new class of chiral complexing agents for NMR spectroscopy, which are able to induce anisochrony of enantiomeric mixtures of apolar trisubstituted allenes and polar derivatized compounds most of which are endowed with a π‐acidic 3,5‐dinitrophenyl ring. The differing contribution to enantiorecognition phenomena of the nature and location of the functional groups on the two cyclodextrin rims was shown. Some interesting aspects of the complexation phenomena, which are the basis of chiral recognition, have been underlined by NMR spectroscopic investigations.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)