Investigation of the chiral recognition by “Brush‐Type” phases in liquid chromatography using crystal structure analyses of diastereomeric 1:1 complexes of a π‐donor and a π‐acceptor derivative of leucine | Zendy

Däppen R. | Zendy; Rihs Grety | Zendy; Mayer Carl W. | Zendy

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Investigation of the chiral recognition by “Brush‐Type” phases in liquid chromatography using crystal structure analyses of diastereomeric 1:1 complexes of a π‐donor and a π‐acceptor derivative of leucine

Author(s) -

Däppen R.,

Rihs Grety,

Mayer Carl W.

Publication year - 1990

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.530020310

Subject(s) - chemistry , diastereomer , enantiomer , elution , derivative (finance) , leucine , chiral derivatizing agent , stereochemistry , acceptor , phase (matter) , crystal structure , monomer , chiral column chromatography , crystallography , chromatography , organic chemistry , amino acid , polymer , biochemistry , physics , financial economics , economics , condensed matter physics

(R,S)‐ N ‐Acetyl‐leucine‐2‐naphthylamide can be resolved into its enantiomers on a (S)‐DNBLeucine chiral stationary phase. The mechanism of this separation was investigated using as model complexes the 1:1 S,S‐ and the 1:1 R,S‐cocrystals of the above naphthylamide and N ‐3,5‐dinitrobenzoylleucinemethylamide, a soluble analogue of the stationary phase. The observed enantiomeric elution order can be rationalized from their X‐ray data.

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