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Host–guest interactions of calix[4]resorcinarenes with benzene derivatives in conditions of reversed‐phase high‐performance liquid chromatography. Determination of stability constants
Author(s) -
Lipkowski J.,
Kalchenko O. I.,
Slowikowska J.,
Kalchenko V. I.,
Lukin O. V.,
Markovsky L. N.,
Nowakowski R.
Publication year - 1998
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199806)11:6<426::aid-poc963>3.0.co;2-r
Subject(s) - resorcinarene , chemistry , acetonitrile , aromaticity , calixarene , resorcinol , phase (matter) , benzene , stability constants of complexes , crystallography , chromatography , molecule , organic chemistry , aqueous solution
Reversed‐phase high‐performance liquid chromatography [LiChrosorb RP‐18,UV detection at 254 nm and acetonitrile‐water (86:14,v/v) as mobile phase] was applied to studies of the host–guest complexation of tetraalkylcalix[4]resorcinareneoctols and their upper rim phosphoryl, sulfonyl and dialkylaminomethyl derivatives with some aromatic guests in the mobile phase. It was shown that the formation of the inclusion complexes results in changes in the retention of aromatic guests and improves their separation. Stability constants of the complexes were calculated from the dependences of the l/ k′ values of the aromatic guest on the concentration of the calix[4]resorcinarene in the mobile phase. The molecular structure of 4,6,16,18‐tetrahydroxy‐10,12,22,24‐tetrakis(dipropoxyphosphoryloxy)‐2,8,14,20‐tetramethylcalix[4]resorcinarene ( 12 ) was determined. Crystal data for 12 are P 2 1 / n, a = 16.708(9) Å, b = 18.683(6) Å, c = 20.243(5) Å, β = 95.75(3)°, V = 6287(4) Å 3 and Z = 4. Compound 12 exists in a boat conformation, in which two opposite unsubstituted resorcinol rings of the macrocyclic skeleton lie in the plane formed by four methine bridges and two diphosphorylated rings are perpendicular to the plane. © 1998 John Wiley & Sons, Ltd.