Collect. Czech. Chem. Commun. 1995, 60, 645-658

Axially Chiral Selectors of C2 Symmetry Bound to Silica: Synthesis and HPLC-Evaluation

Miloš Tichý, Jana Holanová, Ivo Starý, Irena G. Stará and Jiří Závada

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


Axially chiral biaryl stationary phases (CSPs) of C2 symmetry bound to 3-aminopropyl silica both by ionic and covalent bond were prepared. The separation effectivity of the CSPs so obtained was investigated using 2-acylamino alcohols and biaryl derivatives as analytes. Whereas ionically bound phases derived from biphenyl-2,2'-dicarboxylic or 2,2'-bipyridine-3,3'-dicarboxylic acids (CSP 1, 2, 3 and 4) generally exhibited good resolving performance for 2-acylamino alcohols, they were ineffective for biaryl derivatives. On the other hand, covalent CSPs showed poor selector properties with acylamino alcohols; the binaphthyl CSP 7 resolved some of the biaryl analytes. Phase CSP 6 was completely inactive toward all the compounds tested. Absolute configuration of 4,4',6,6'-tetranitrobiphenyl-2,2'-dicarboxylic acid (II) has been derived from its CD spectrum and some speculations on configuration of bipyridine diacid IV are presented.