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Pregled bibliografske jedinice broj: 525743

Mechanism of chiral recognition in the enantioseparation of 2-aryloxypropionic acids on new brush-type chiral stationary phases


Vinković, Vladimir; Kontrec, Darko; Šunjić, Vitomir; Navarini, Luciano; Zanetti, Flavio; Azzolina, Ornella
Mechanism of chiral recognition in the enantioseparation of 2-aryloxypropionic acids on new brush-type chiral stationary phases // Chirality, 13 (2001), 9; 581-587 doi:10.1002/chir.1181 (međunarodna recenzija, članak, znanstveni)


Naslov
Mechanism of chiral recognition in the enantioseparation of 2-aryloxypropionic acids on new brush-type chiral stationary phases

Autori
Vinković, Vladimir ; Kontrec, Darko ; Šunjić, Vitomir ; Navarini, Luciano ; Zanetti, Flavio ; Azzolina, Ornella

Izvornik
Chirality (0899-0042) 13 (2001), 9; 581-587

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Chiral stationary phase; 2-aryloxypropionic acid; enantioseparation; HPLC

Sažetak
New brush-type chiral stationary phases (CSP I-IV) comprising N-3, 5, 6-trichloro-2, 4-dicyanophenyl-L-alpha-amino acids (1-4) were prepared by binding of chiral selectors 1-4 to gamma-aminopropyl silica gel. To check the role of excess free aminopropyl groups, CSP V was prepared by binding N-3, 5, 6-trichloro-2, 4-dicyanophenyl-L-alanyl-(3-triethoxysilyl)propylamide to unmodified silica gel. The best separation of racemic 2-aryloxypropionic acids (TR-1-13) was obtained with CSP I ; the -(-)-S enantiomer were regularly eluted first, as determined by a CD detector. The mechanism of chiral recognition implies a synergistic interaction of carboxylic acid analyte with the chiral selector and achiral free gamma-aminopropyl units on silica. In fact, CSP V, which is lacking an achiral aminopropyl spacer, shows a lower separation ability for 2-aryloxypropionic acids, but a similar enantioselective discrimination of esters TR-19-20, in comparison with CSP I. CSP I-IV retain unaltered separation ability after a few months of continuous work using a large number of various mobile phases.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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