HOST-GUEST INTERACTIONS OF CALIX[4B]RESORCINARENES WITH BENZENE-DERIVATIVES IN CONDITIONS OF REVERSED-PHASE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY - DETERMINATION OF STABILITY-CONSTANTS

Reversed-phase high-performance liquid chromatography [LiChrosorb RP-. 18,UV detection at 254 Mn and acetonitrile-water (86:14,v/v) as mobile phase] was applied to studies of the host-guest complexation of tetra alkylcalix[4]resorcinareneoctols and their upper rim phosphoryl, sulfo nyl and dialkylaminomethyl derivatives with some aromatic guests in th e mobile phase. It was shown that the formation of the inclusion compl exes results in changes in the retention of aromatic guests and improv es their separation. Stability constants of the complexes were calcula ted from the dependences of the l/k' values of the aromatic guest on t he concentration of the calix[4]resorcinarene in the mobile phase. The molecular structure of ryloxy)-2,8,14,20-tetramethylcalix[4]resorcina rene (12) was determined. Crystal data for 12 are P2(1)/n, a = 16.708( 9) Angstrom, b = 18.683(6) Angstrom, c = 20.243(5) Angstrom, beta = 95 .75(3)degrees, V = 6287(4) Angstrom(3) and Z = 4. Compound 12 exists i n a boat conformation, in which two opposite unsubstituted resorcinol rings of the macrocyclic skeleton lie in the plane formed by four meth ine bridges and two diphosphorylated rings are perpendicular to the pl ane. (C) 1998 John Wiley & Sons, Ltd.