INTERACTION OF CALYX[4]RESORCINONS CARRYING AN ALKYL RADICAL AT THE LOWER «RIM» OF THE MOLECULE WITH DIPHENYLPHOSPHORYLACACETIC ACID HYDRAZIDE

Macrocyclic compounds - calixresorcins - are a cavity system with a rigid cup-shaped cavity containing four resorcinol rings, which provide a π-electron-rich cavity and polar hydroxyl groups at the upper rim of the resorcinol[4]arene. In this paper, we present data on the production of «guest-host» complexes of C - alkylated calixresorcins in the armchair conformation with Phosenazide - ([2-(diphenylphosphoryl)acetohydrazide]), which exists in the form of two crystalline modifications I and II. NMR, UV and IR spectroscopy methods were used to assess the nature of the interaction between calixresorcins and Phosenazide. The composition of the isolated complexes was determined by the method of elemental analysis. According to the data of the elemental analysis, the ratio of «guest» and «host» in all selected complexes is the same and is 2:1. The nature of the interaction is in all cases hydrogen bonding between the P=O and C=O groups of two «guest» molecules of Phosenazide and hydroxyl groups of one «host» of calixresorcinol. The length of the alkyl radical along the lower «rim» of calixresorcins affects the degree of participation of these groups in the interaction process and a certain difference in structures. The long alkyl radicals C9H19 and C7H15 along the lower «rim» of calixresorcinol make the cavity less rigid compared to calixresorcinol, which carries the CH3 radical along the lower «rim». Therefore, in the case of calix[4]resorcins with C9H19 and C7H15 radicals, a modification of Phosenazide II is involved in the interaction, which is characterized by weak participation in hydrogen binding of both Phosenazide and calix[4]resorcins. On the contrary, in the case of the formation of the calix[4]resorcinol complex with the CH3 radical modification of Phosenazide I is observed. Each of the «guest» molecules provides four binding centers capable of forming hydrogen bonds with eight hydroxyl groups of calix[4]resorcinol.