High-Performance liquid chromatographic enantioseparation of atropisomeric biphenyls on seven chiral stationary phases

Current Organic Chemistry

Volumn 15, Issue 8, 2011, Pages 1208-1229

  Peluso, Paola ^a   Fabbri, Davide ^a   Dettori, Maria Antonietta ^a   Delogu, Giovanna ^a   Zambrano, Vincenzo ^a   Cossu, Sergio ^b  

^a UNIVERSITY OF SASSARI   (Italy)

^b CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

Atropisomeric biphenyls; Enantiomeric separation; High performance liquid chromatography; Molecular recognition; Polymetacrylate stationary phases; Polysaccharide stationary phases

Indexed keywords

ETHANOL; HEXANE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ATROPISOMERIC BIPHENYL; CHIRAL SELECTOR; CHIRALCEL OD-H; ENANTIOMERIC SEPARATION; ENANTIOSEPARATIONS; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; POLYMETACRYLATE STATIONARY PHASE; POLYSACCHARIDE STATIONARY PHASE; STATIONARY PHASE;

CELLULOSE;

EID: 79953312677     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211795203068     Document Type: Article

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54. This effect was observed not only for unsymmetric substituted 10 and 11, but also for symmetric 1, 6, 7, 8, 9, 3. Taking into account that the dipole moment varies with the conformation of biphenyls and that the dipole of each ring can influence the conformation of biphenyl [53], the orthogonal geometry minimizes the steric interactions between ortho substituents but at expense of π-electron overlap. In this situation the unsymmetrical distribution of electron density in the near-orthogonal geometry can be related to the decreased π-electron overlap and, thus, to a sort of compensation to minimize the dipole moment.