The interaction in aqueous solution of the cyclophane receptors 2,6,10,13,1
7,21-hexaaza[22]orthocyclophane (L-1) and 2,6,10,13,17,21-hexaaza[22]paracy
clophane (L-2) with the nucleotides ATP, ADP and AMP has been studied by pH
titration and NMR. The obtained results are compared with those previously
reported for the analogous meta-substituted receptor 2,6,10,13,17,21-hexaa
za[22]metacyclophane (L). All the experimental data support the actuation o
f these cyclophane molecules as multi-point binders of nucleotides through
electrostatic, hydrogen bonding and pi-stacking interactions. The combined
use of NMR and molecular dynamics permits us to get a rather reliable pictu
re of the way in which the molecules organise in solution and how the inter
molecular interactions (electrostatics, hydrogen bonding, pi-stacking) are
established.