Influence of the nature of alkyl substituents on the high-performance liquid chromatography enantioseparation and retention of new atropisomeric 1,1′-bibenzimidazole derivatives on amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase
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Abstract
Six new atropisomeric heteroarenes were synthesized by connecting two 2-alkylbenzimidazole
fragments via N-N junction. They differ by the substituent nature (methyl, ethyl,
propyl, butyl, pentyl and hexyl) of the aliphatic function. The novel atropisomeric
compounds were used as chiral probes to study the chromatographic behavior of the
amylose tris(3,5-dimethylphenyl carbamate) (Chiralpak AD-3) chiral stationary phase
(CSP) under normal phase mode. The pivotal role of the length and flexibility of the
2,2'-alkyl groups on retention, enantioselectivity and enantiomer elution order was
demonstrated by enantioselective HPLC analysis. Additional information on the chiral
recognition mechanism was obtained from the evaluation of the correlated thermodynamic
data.