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all ‐Homocalixarene: Carbocyclische Wirtverbindungen mit intra‐ und extraannularen Ligandarmen
Author(s) -
Schmitz Jürgen,
Vögtle Fritz,
Nieger Martin,
Gloe Karsten,
Stephan Holger,
Heitzsch Olaf,
Buschmann HansJürgen,
Hasse Wolfgang,
Cammann Karl
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931261123
Subject(s) - chemistry , pentamer , molecule , extraction (chemistry) , metal ions in aqueous solution , stereochemistry , ligand (biochemistry) , selectivity , calixarene , solvent , medicinal chemistry , crystallography , metal , organic chemistry , biochemistry , receptor , catalysis
all ‐Homocalixarenes: Carbocyclic Host Compounds with Intra‐ and Extraannular Ligand Arms Methoxy‐substituted [2 n ]metacyclophanes 1–10 , obtained by Müller‐Röscheisen cyclization, are converted into all ‐homocalixarenes 11–20 with free phenolic hydroxy functions. The well‐soluble cyclic pentamer 11 and octamer 14 with endo‐acidic host properties are investigated with regard to guest binding. They exhibit selectivity towards alkaline earth metal ions (Ba 2+ ) in liquid/liquid extraction studies. Some of the macrocyclic oligophenols are transformed into homocalixarenes 21–25 with intra‐ or extraannular oxapropionate groups. The diester 22 and the tetraester 23 are converted into carbocycles 26 and 27 with two and four free oxapropionic acid groups. Complexation properties of the oligoesters in extraction studies and log K values in water are reported. X‐ray structural analyses were performed of the [6]‐, [8]‐ and [4]‐ homocalixarenes 9 and 21, 14 and 23 ; the inclusion of solvent molecules is proven.