Different partitioning behaviour of sulphonyl-containing compounds in reversed-phase high-performance liquid chromatography and octanol-water systems

The lipophilicities of 27 monosubstituted benzene derivatives bearing sulphonyl, carbonyl and other polar substituents were measured by two reversed-phase high-performance liquid chromatographic (RP-HPLC) methods, in the presence and absence of n-decylamine as a masking agent. The results were compa...

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Bibliographic Details
Published in:Journal of Chromatography A 1988, Vol.439 (2), p.237-244
Main Authors: El Tayar, Nabil, Tsantili-Kakoulidou, Anna, Roethlisberger, Thierry, Testa, Bernard, Gal, Joseph
Format: Article
Language:English
Subjects:
Analytical chemistry
Chemistry
Chromatographic methods and physical methods associated with chromatography
Exact sciences and technology
Other chromatographic methods
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Summary:The lipophilicities of 27 monosubstituted benzene derivatives bearing sulphonyl, carbonyl and other polar substituents were measured by two reversed-phase high-performance liquid chromatographic (RP-HPLC) methods, in the presence and absence of n-decylamine as a masking agent. The results were compared with literature n-octanol-water partition coefficients, showing that compounds with strong hydrogen-bond accepting groups have log k w values that are considerably higher than expected from their log P oct values. This deviant partitioning behaviour in RP-HPLC is attributed to strong adsorption on free silanol groups. A comparison with retention data on a silica gel stationary phase and with the hydrogen-bond acceptor basicity parameter (β) validated this hypothesis.
ISSN:0021-9673
DOI:10.1016/S0021-9673(01)83837-1