Synthesis and protonation behaviour of the macrocycle 2,6,10,13,17,21-hexaaza[22]metacyclophane. Thermodynamic and NMR studies on the interaction of 2,6,10,13,17,21-hexaaza[22]metacyclophane and on the open-chain polyamine 4,8,11,15-tetraazaoctadecane-1,18-diamine with ATP, ADP and AMP

Abstract The novel cyclophane receptor 2,6,10,13,17,21-hexaaza[22]metacyclophane (L) has been synthesised and characterised. The acid-base behaviour and interaction with ATP, ADP and AMP have been studied by potentiometry in 0.15 mol dm−3 at 298.1 K and multinuclear NMR. L presents in its protonated forms a molecular organization which enables its multipoint binding with nucleotides. Salt-bridge formation occur between the polyammonium sites of L and the phosphate chain of the nucleotides while π-stacking between the meta-phenylene subunit incorporated in the receptor and the adenine ring of the nucleotides.