Mc. Rotger et al., A CYCLOPHANE RECEPTOR FOR THE SELECTIVE COMPLEXATION OF ADENINE-DERIVATIVES IN WATER, Journal of organic chemistry, 59(16), 1994, pp. 4501-4505
A water-soluble oxacyclophane based upon p-xylylenebis[4-hydroxy-3-car
boxybenez] and p-xylene units tethered trough an aliphatic chain has b
een synthesized. The receptor binds selectively to neutral adenine der
ivatives forming an intracavity 1:1 complex. The interaction energies
for the complexes range from 7 to 13 kJ mol(-1) in alkaline D2O. The g
eometry of the complex between 1(dicarboxylate) and 9-ethyladenine has
been mapped out through NMR studies and is also supported by molecula
r modeling and theoretical AM1 calculations.