1994
DOI: 10.1016/0021-9673(94)00595-8
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Mechanistic evaluation of the resolution of α-amino acids on dynamic chiral stationary phases derived from amino alcohols by ligand-exchange chromatography

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Cited by 26 publications
(18 citation statements)
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“…4). In this model, which parallels previously reported examples, 15,27 the chiral selector is bound to the octadecyl-silica gel through the hydrophobic interaction of the benzyl group and the sulfur atom intercalated between the RP-18 carbon chains of the original stationary phase. Cu(II) is then coordinated by the bounded chiral selector and the analyte, thus producing a ternary complex that can be completed by two axial water molecules (not shown).…”
Section: Mechanism Of Chiral Recognitionsupporting
confidence: 58%
“…4). In this model, which parallels previously reported examples, 15,27 the chiral selector is bound to the octadecyl-silica gel through the hydrophobic interaction of the benzyl group and the sulfur atom intercalated between the RP-18 carbon chains of the original stationary phase. Cu(II) is then coordinated by the bounded chiral selector and the analyte, thus producing a ternary complex that can be completed by two axial water molecules (not shown).…”
Section: Mechanism Of Chiral Recognitionsupporting
confidence: 58%
“…3). In this model, which parallels previously reported examples [2,26,28], the chiral selector is bound to the octadecyl-silica gel through the hydrophobic interaction of the naphthyl groups intercalated between the RP-18 carbon chains of the original stationary phase. Cu(II) is then co-ordinated by the bounded chiral selector and the analyte, thus producing a ternary complex that can be completed by two axial water molecules (not shown).…”
Section: Resultsmentioning
confidence: 51%
“…24 Relative positive charge surface area: solvent-accessible surface area of the most positive atom divided by descriptor 22 (RPCS). 26 Total hydrophobic surface area: sum of solvent-accessible surface areas of atoms with absolute value of partial charges less than 0.2 (TASA) 27 Total polar surface area: sum of solvent-accessible surface areas of atoms with absolute value of partial charges greater than or equal to 0.2 (TPSA). 28 Relative hydrophobic surface area: total hydrophobic surface area divided by the total molecular solvent-accessible surface area (RASA).…”
Section: -21mentioning
confidence: 99%
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“…Several selectors have been used so far, mostly amino acid derivatives, lPl6 although other optically active materials have also been proposed. [17][18][19] In a systematic approach aimed at studying the mechanism of chiral separation, we developed a series of chiral selectors derived from amino acids, which were able to separate Dnsamino acids, 2o unmodified amino acids, 21 and hydroxy acidsz2 in HPLC with good enantioselectivity factors. Moreover, we have shown that with bis(amino acid amidato)copper(II) complexes added to the eluent, ligand exchange is actually occurring in the chromatographic system, leading to formation of the ternary diastereomeric complexes and displacement of one ligand.…”
Section: Introductionmentioning
confidence: 99%