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  • 1
    Electronic Resource
    Electronic Resource
    The influence of solute structure, temperature, and eluent composition on the chiral separation of 21 aminotetralins on a cellulose tris-3,5-dimethylcarbamate stationary phase in high-performance liquid chromatography (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 4 (1992), S. 389-394 
    Details
    ISSN: 0899-0042
    Keywords: chiral stationary phase ; CHIRALCEL OD ; temperature effect ; enantiomeric separation ; aminotetralins ; dopamine agonists ; resolution ; chiral recognition mechanism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In the present study 21 different chiral aminotetralins were used to investigate the mechanism behind their enantiomeric resolution (Rs) on a commercially available high-performance liquid chromatography (HPLC) cellulose tris-3,5-dimethylcarbamate stationary phase. The differences in the chemical structures of the aminotetralins used were never directly located on the chiral carbon. Their chromatographic behavior was studied for two eluent compositions at six different temperatures. Hydrogen bonding and π—π interactions are two possible solute-chiral stationary phase (CSP) interactions. Differences between the enantiomers in their spatial arrangement of positions involved in solute-CSP interactions were the major forces behind enantiomeric separation.Lowering the temperature increased the Rs for the aminotetralins having π-electrons not directly bonded to that part of the molecule where the hydrogen bonding with the CSP is located. Primary amines and secondary amines, with a sufficiently short N-alkyl substituent, showed a decrease of Rs with lower temperatures, all other aminotetralins yielding an increase of Rs with lower temperatures. © 1992 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530040610
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  • 2
    Electronic Resource
    Electronic Resource
    Comparison between cellulose and amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phases for enantiomeric separation of 17 amidotetralins (1993)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 5 (1993), S. 545-553 
    Details
    ISSN: 0899-0042
    Keywords: cellulose ; amylose ; silica gel ; high performance liquid chromatography ; direct separations ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Direct enantiomeric separations of 17 chiral amidotetralins by means of high performance liquid chromatography were performed on stationary phases composed of tris(3,5-dimethylphenylcarbamate) derivatives of cellulose and amylose, coated on silica gel. The enantiomers of 15 out of 17 amidotetralins were resolved with a resolution of more than 1.5 by at least one of the chiral stationary phases. The stationary phases showed complementary results with regard to the separation of the amidotetralins, that is, pairs that did not separate on the cellulose-type column were well separated on the amylose-type column, and vice versa. There was no significant correlation between the chromatographic properties of the chiral stationary phases. © 1993 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530050711
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