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  • quantitative substituent effects  (2)
  • Atropisomerism  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Separation of N-arylthiazoline-2-(thi)-one atropisomers on p-methylbenzoyl cellulose beads: A factorial design approach (1993)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 5 (1993), S. 207-212 
    Details
    ISSN: 0899-0042
    Keywords: chiral HPLC ; solvent effect ; quantitative substituent effects ; molecular recognition mechanism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A two level full factorial design has been applied to quantify the effect of three selected structural parameters on the capacity factors and chiral separation of atropisomers in N-arylthiazoline-2-(thi)-ones derivatives on tris(p-methylbenzoyl) cellulose beads. The behavior of the two enantiomers is influenced by different factors which might result from different retention sites within the same stationary phase. It appears that the two enantiomers behave independently on the CSP, the order of elution and separation being controlled by a minor steric modification in a very precise location in the molecule for one enantiomer. The methodology of the experimental design allows the comparison of equations generated from data issued from designed compounds. These equations afford much more information than the step by step comparison of individual molecules. In our case, the tris(p-methylbenzoyl)cellulose beads and microcrystalline cellulose triacetate appear as complementary CSPs for the resolution of atropisomers of the series studied. © 1993 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530050403
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  • 2
    Electronic Resource
    Electronic Resource
    Effects of alkyl substituents on chiral separation of N-arylthiazolin-2-(thi)-one atropisomers on tris (p-methylbenzoyl)cellulose beads and cellulose triacetate: Lipophilicity aspects (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 6 (1994), S. 251-260 
    Details
    ISSN: 0899-0042
    Keywords: chiral HPLC ; experimental design ; quantitative substituent effects ; recognition mechanism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The determination of lipophilicity of the title compounds allowed treatment of the data for chiral separation (capacity factors) on CTA and CTPB according to these parameters. A linear correlation between In k′(+) and log k′w was found on both CTA and CTPB, as far as the substituents are situated in the plane of the aryl ring or the heterocycle. This correlation with a nonchiral descriptor allows treatment of capacity factors for (-)-enantiomers as deviations from the lipophilicity line or derived parallels. It results in a clear description of the molecular area affecting enantioselectivity. Application to larger alkyl derivatives shows that the effect of the substituent should be treated on a basis of attractive effect in the case of CTA and on the basis of attractive and repulsive effects for CTPB. © 1994 Wiley-Liss, Inc.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530060407
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  • 3
    Electronic Resource
    Electronic Resource
    Bis[oxo/thioxothiazolinyl] Aromatic Compounds - Synthesis and Conformational Assignment (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1081-1090 
    Details
    ISSN: 1434-193X
    Keywords: Atropisomerism ; Conformation analysis ; Liquid chromatography ; Chiral resolution ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---A series of bis(oxo/thioxothiazolinyl) aromatic atropisomers with two chiral C(aryl)-N(heterocycle) axes was synthesized. The separation of antiparallel, parallel diastereomers was achieved by chromatography on silica. Conformational assignment for the bis-thione atropisomers 1a,b-4a,b and bis-one atropisomers 9a,b-12a,b was based on polarimetric results in analytical chiral chromatography on microcrystalline cellulose triacetate. The relationship conformation-1H NMR chemical shifts, found for the bis-thiones and bis-ones was successfully applied for the conformational assignment of thione-one atropisomers not assigned by chiral liquid chromatography.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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