Bidentate urea-based chiral selectors for enantioselective high performance liquid chromatography: Synthesis and evaluation of \"Crab-like\" stationary phases (Articolo in rivista)

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  • Bidentate urea-based chiral selectors for enantioselective high performance liquid chromatography: Synthesis and evaluation of \"Crab-like\" stationary phases (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.chroma.2013.04.083 (literal)
Alternative label
  • D. Kotoni, C. Villani, D. S Bell, D. Capitani, P. Campiglia, F. Gasparrini (2013)
    Bidentate urea-based chiral selectors for enantioselective high performance liquid chromatography: Synthesis and evaluation of "Crab-like" stationary phases
    in Journal of chromatography (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • D. Kotoni, C. Villani, D. S Bell, D. Capitani, P. Campiglia, F. Gasparrini (literal)
Pagina inizio
  • 157 (literal)
Pagina fine
  • 167 (literal)
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  • http://dx.doi.org/10.1016/j.chroma.2013.04.083 (literal)
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  • 1297 (literal)
Rivista
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  • 11 (literal)
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  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
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  • Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma Sigma Aldrich Supelco, Bellefonte, PA 16823 USA Istituto di Metodologie Chimiche, CNR Area della Ricerca di Roma, 00015 Monterotondo (RM) Univ Salerno, Dipartimento Sci Farmaceut & Biomed, I-84084 Salerno, Italy (literal)
Titolo
  • Bidentate urea-based chiral selectors for enantioselective high performance liquid chromatography: Synthesis and evaluation of \"Crab-like\" stationary phases (literal)
Abstract
  • A rational approach for the design and preparation of two new \"Crab-like\" totally synthetic, brush-type chiral stationary phases is presented. Enantiopure diamines, namely 1,2-diaminocyclohexane and 1,2-diphenyl-1,2-ethylene-diamine were treated with 3-(triethoxysilyl)propyl isocyanate, to yield reactive ureido selectors that were eventually attached to unmodified silica particles through a stable, bidentate tether, through a facile two-step one-pot procedure. A full chemical characterization of the new materials has been obtained through solid-state NMR (both Si-29 and C-13 CPMAS) spectroscopy. Columns packed with the two Crab-like chiral stationary phases allow for different mechanisms of separation: normal phase liquid chromatography, reversed phase liquid chromatography and polar organic mode and show a high stability at basic pH values. In particular, the Crab-like column containing the 1,2-diphenyl-1,2-ethylene-diamine selector proved a promising candidate for the resolution of a wide range of racemates (including benzodiazepines, N-derivatized amino acids, and free carboxylic acids) both in normal phase and polar organic mode. An H-min of 9.57 at a mu(sf) of 0.80 mm/s (corresponding to 0.8 mL/min) was obtained through van Deemter analysis, based on toluene, for the Crab-like column with the 1,2-diphenyl-1,2-ethylene-diamine selector (250 mm x 4.6 mm I.D.), with a calculated reduced height equivalent to a theoretical plate (h) of only 1.91. Finally, comparative studies were performed with a polymeric commercially available P-CAP-DP column in order to evaluate enantioselectivity and resolution of the Crab-like columns (literal)
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