Abstract
AbstractIn 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.
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