High-performance liquid chromatographic enantioseparation of naphthol-substituted tetrahydroisoquinolines on polysaccharide-based chiral stationary phases

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Abstract

The stereoisomers of 15 naphthol-substituted tetrahydroisoquinoline analogs were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenyl carbamate) (Cellulose 1), cellulose tris-(3-chloro-4-methylphenyl carbamate) (Cellulose 2), cellulose tris-(4-methylbenzoate) (Cellulose 3) and cellulose tris-(4-chloro-3-methylphenyl carbamate) (Cellulose 4). Experiments were performed in normal-phase mode with n-heptane(n-hexane)-alcohol-diethylamine mobile phases in the temperature range 5-40°C. Thermodynamic parameters were calculated from plots of lnk or lnα vs 1/T. On the Cellulose 1 column, Δ(ΔH°) ranged from -6.8 to 5.9kJ/mol, Δ(ΔS°) from -16.7 to 21.0J/mol/K and the Gibbs energy, -Δ(ΔG°) from 0.2 to 1.5kJ/mol; on the Cellulose 2 column, Δ(ΔH°) ranged from -7.8 to 2.5kJ/mol, Δ(ΔS°) from -16.1 to 13.2J/mol/K and-Δ(ΔG°) from 0.7 to 3.0kJ/mol. Both enthalpy- and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature.

Original languageEnglish
Pages (from-to)142-151
Number of pages10
JournalBiomedical Chromatography
Volume28
Issue number1
DOIs
Publication statusPublished - Jan 2014

Fingerprint

Tetrahydroisoquinolines
Naphthols
Cellulose
Polysaccharides
Liquids
Carbamates
Stereoisomerism
Temperature
Entropy
Thermodynamics
Gibbs free energy
Enthalpy
Alcohols

Keywords

  • Direct enantiomer separation of naphthol-substituted tetrahydroisoquinoline analogs
  • High-performance liquid chromatography (HPLC)
  • Temperature dependence of chiral separation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Pharmacology

Cite this

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title = "High-performance liquid chromatographic enantioseparation of naphthol-substituted tetrahydroisoquinolines on polysaccharide-based chiral stationary phases",
abstract = "The stereoisomers of 15 naphthol-substituted tetrahydroisoquinoline analogs were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenyl carbamate) (Cellulose 1), cellulose tris-(3-chloro-4-methylphenyl carbamate) (Cellulose 2), cellulose tris-(4-methylbenzoate) (Cellulose 3) and cellulose tris-(4-chloro-3-methylphenyl carbamate) (Cellulose 4). Experiments were performed in normal-phase mode with n-heptane(n-hexane)-alcohol-diethylamine mobile phases in the temperature range 5-40°C. Thermodynamic parameters were calculated from plots of lnk or lnα vs 1/T. On the Cellulose 1 column, Δ(ΔH°) ranged from -6.8 to 5.9kJ/mol, Δ(ΔS°) from -16.7 to 21.0J/mol/K and the Gibbs energy, -Δ(ΔG°) from 0.2 to 1.5kJ/mol; on the Cellulose 2 column, Δ(ΔH°) ranged from -7.8 to 2.5kJ/mol, Δ(ΔS°) from -16.1 to 13.2J/mol/K and-Δ(ΔG°) from 0.7 to 3.0kJ/mol. Both enthalpy- and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature.",
keywords = "Direct enantiomer separation of naphthol-substituted tetrahydroisoquinoline analogs, High-performance liquid chromatography (HPLC), Temperature dependence of chiral separation",
author = "I. Ilisz and Zsanett Gecse and I. Szatm{\'a}ri and F. F{\"u}l{\"o}p and A. P{\'e}ter",
year = "2014",
month = "1",
doi = "10.1002/bmc.3002",
language = "English",
volume = "28",
pages = "142--151",
journal = "Biomedical Chromatography",
issn = "0269-3879",
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T1 - High-performance liquid chromatographic enantioseparation of naphthol-substituted tetrahydroisoquinolines on polysaccharide-based chiral stationary phases

AU - Ilisz, I.

AU - Gecse, Zsanett

AU - Szatmári, I.

AU - Fülöp, F.

AU - Péter, A.

PY - 2014/1

Y1 - 2014/1

N2 - The stereoisomers of 15 naphthol-substituted tetrahydroisoquinoline analogs were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenyl carbamate) (Cellulose 1), cellulose tris-(3-chloro-4-methylphenyl carbamate) (Cellulose 2), cellulose tris-(4-methylbenzoate) (Cellulose 3) and cellulose tris-(4-chloro-3-methylphenyl carbamate) (Cellulose 4). Experiments were performed in normal-phase mode with n-heptane(n-hexane)-alcohol-diethylamine mobile phases in the temperature range 5-40°C. Thermodynamic parameters were calculated from plots of lnk or lnα vs 1/T. On the Cellulose 1 column, Δ(ΔH°) ranged from -6.8 to 5.9kJ/mol, Δ(ΔS°) from -16.7 to 21.0J/mol/K and the Gibbs energy, -Δ(ΔG°) from 0.2 to 1.5kJ/mol; on the Cellulose 2 column, Δ(ΔH°) ranged from -7.8 to 2.5kJ/mol, Δ(ΔS°) from -16.1 to 13.2J/mol/K and-Δ(ΔG°) from 0.7 to 3.0kJ/mol. Both enthalpy- and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature.

AB - The stereoisomers of 15 naphthol-substituted tetrahydroisoquinoline analogs were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenyl carbamate) (Cellulose 1), cellulose tris-(3-chloro-4-methylphenyl carbamate) (Cellulose 2), cellulose tris-(4-methylbenzoate) (Cellulose 3) and cellulose tris-(4-chloro-3-methylphenyl carbamate) (Cellulose 4). Experiments were performed in normal-phase mode with n-heptane(n-hexane)-alcohol-diethylamine mobile phases in the temperature range 5-40°C. Thermodynamic parameters were calculated from plots of lnk or lnα vs 1/T. On the Cellulose 1 column, Δ(ΔH°) ranged from -6.8 to 5.9kJ/mol, Δ(ΔS°) from -16.7 to 21.0J/mol/K and the Gibbs energy, -Δ(ΔG°) from 0.2 to 1.5kJ/mol; on the Cellulose 2 column, Δ(ΔH°) ranged from -7.8 to 2.5kJ/mol, Δ(ΔS°) from -16.1 to 13.2J/mol/K and-Δ(ΔG°) from 0.7 to 3.0kJ/mol. Both enthalpy- and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature.

KW - Direct enantiomer separation of naphthol-substituted tetrahydroisoquinoline analogs

KW - High-performance liquid chromatography (HPLC)

KW - Temperature dependence of chiral separation

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JO - Biomedical Chromatography

JF - Biomedical Chromatography

SN - 0269-3879

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