Structural and conformational features of "heterogeneous" naphthophosphacyclophanes on the basis of 1,6-dihydroxynaphthalene

The aim of this research was to carry out computer modeling of "heterogeneous" naphthophosphacyclophanes synthesized by molecular integration. One of the structural units is represented by asymmetric 1,6-dihydroxynaphthalene, and the other one is based on dihydroxynaphtalene with the most remoted in space hydroxogroups (1,7-, 2,6-and 2,7-dihydroxynaphthalenes). Amides of phosphite with different substituents at the phosphorus atom perform as an aliphatic linker in macrocyclic systems. Moreover, we calculated the equilibrium geometry of the molecules of synthesized "heterogeneous" naphthophosphacyclophanes and we applied RM1 semiemperical method and quantum-chemical calculations ab initio HF (3-21G). Based on comparative analysis of ¹H and ³¹P NMR spectroscopy data as well as semi-empirical method RM1 data, we determined the optimal configuration of the synthesized naphthocyclophanes. The findings of the research show that the mutual arrangement of aromatic fragments depends on structural features of initial dihydroxynaphthalenes.

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