Premium
Interactions of chiral molecules with an (r)‐ n ‐(3,5‐dinitrobenzoyl) phenylglycine HPLC stationary phase
Author(s) -
Berthod Alain,
Jin Heng Liang,
Stalcup Apryll M.,
Armstrong Daniel 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.530020106
Subject(s) - chemistry , chiral derivatizing agent , enantiomer , steric effects , chiral column chromatography , chiral stationary phase , chirality (physics) , high performance liquid chromatography , stereochemistry , molecule , phase (matter) , chromatography , organic chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
Forty different chiral molecules were studied by liquid chromatography with a Pirkle‐type, (R)‐ N ‐(3,5‐dinitrobenzoyl) phenylglycine (DNBPG), chiral stationary phase column. The dramatic effect of a small molecular change on chiral recognition was demonstrated using DL‐amino acid derivatives. The inductive effect on chiral recognition was also studied using trifluoro‐, trichloro‐, dichloro‐, monochloroacetyl, and acetyl derivatives of four different chiral amines. The study of the enantiomer separation of 11 different crown ethers of 2,2′‐binaphthyldiyl showed that the rigidity of the chiral center can be an additional parameter in chiral recognition for the DNBPG phase but not for a β‐cyclodextrin bonded chiral phase. It is apparent from this study that steric effects, inductive effects, and molecular rigidity play important roles in chiral recognition with DNBPG chiral stationary phases.