ISSN:
0899-0042
Keywords:
chiral HPLC
;
quantitative substituent effect
;
recognition mechanism
;
fluorene derivative-chiral separation
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The chromatographic parameters for 12 structurally related compounds in the 4a-methyl-2,3,4,4a-tetrahydro-1H-fluorene and 4a-methyl-1,2,3,4,4a,9a-hexahydro-fluoren-9-one series are reported on CTA-I and Chiralcel OJ chiral stationary phases. Arrangement of the k' values according to configurationally related enantiomer series (Class I and Class II) and not according to the actual order of elution, allows the treatment of the data by linear correlation with structure and substituent effect. A detailed analysis of the capacity factor variation with respect to the structural changes shows clearly that the framework and substitution effects do not result in the same response on the two cellulose ester chiral stationary phases. More interestingly, it emerges that chiral discimination may be attributed to certain areas of the molecule, these areas being different in the interaction within CTA-I and Chiralcel OJ. Furthermore, our analysis points out the relevance of attempting to develop quantitative relationships for configurationally related series of enantiomers (in our case Class I and Class II), the main effort being devoted to the understanding of the capacity factor variation in each class rather than of the α values, which are derived entities. Chirality 10:522-527, 1998. © 1998 Wiley-Liss, Inc.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
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