title: 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.
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.
authors.affiliation: Ist. di Scienze e Tecnologie Molecolari, Consiglio Nazionale delle Ricerche, via Golgi 19, 20133 Milano, Italy.
authors.forename: Simona
authors.initials: S
authors.lastname: Rizzo
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Piazzale A. Moro 5, I-00185 Roma, Italy.
authors.forename: Sergio
authors.initials: S
authors.lastname: Menta
authors.affiliation: Università degli studi di Firenze, Dipartimento di Chimica, Via della Lastruccia 13, 50019 Sesto Fiorentino, Firenze, Italy.
authors.forename: Cristina
authors.initials: C
authors.lastname: Faggi
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Piazzale A. Moro 5, I-00185 Roma, Italy. Electronic address: marco.pierini@uniroma1.it.
authors.forename: Marco
authors.initials: M
authors.lastname: Pierini
authors.affiliation: Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, I-00161 Roma, Italy. Electronic address: rcirilli@iss.it.
authors.forename: Roberto
authors.initials: R
authors.lastname: Cirilli
mesh_terms: D002219:Carbamates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D002219:Carbamates
keywords: Chiral stationary phase; Chiralpak AD-3; Enantiomer elution order; Enantiomer separation; Isoenantioselective temperature; Thermodynamic parameters