Isotope Effects on the Lipophilicity of Deuterated Caffeines
| Autor: | Bernard Testa, Youssef Benchekroun, Jean-Louis Brazier, Jean-Bernard Falconnet, Antoine Bechalany, Nabil El Tayar, Pierre-Alain Carrupt, Yahia Cherrah |
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| Rok vydání: | 1989 |
| Předmět: |
ddc:615
Chemistry Stereochemistry Organic Chemistry Biochemistry Medicinal chemistry Catalysis Isotopomers Inorganic Chemistry chemistry.chemical_compound Deuterium Intramolecular force Drug Discovery Lipophilicity Kinetic isotope effect Structural isomer Electronic effect Physical and Theoretical Chemistry Caffeine |
| Zdroj: | Helvetica Chimica Acta, Vol. 72, No 3 (1989) pp. 472-476 |
| ISSN: | 1522-2675 0018-019X |
| Popis: | In the present study, it is confirmed that the deuteration of CH groups is accompanied by a small but genuine decrease in lipophilicity. The lipophilicity of deuterated isotopomers of caffeine was measured by reversed-phase HPLC. Overall, lipophilicity was shown to decrease when going from unlabelled caffeine to the three isomeric trideuterated caffeines, then to the three isomeric hexadeuterated caffeines, and finally to nonadeuterated caffeine. In addition, position-specific effects were also proven. E.g. (7-methyl-2H3)caffeine experienced a smaller isotope effect than its two positional isomers. Both a cavity factor (decreased volume of deuterated isotopomers) and intramolecular electronic effects are postulated to operate. |
| Databáze: | OpenAIRE |
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