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A water‐soluble tetraoxa[7.1.7.1]paracyclophane: Synthesis and host‐guest interactions with alicyclic and cationic aromatic guest molecules in aqueous solution
Author(s) -
Diederich François,
Dick Klaus
Publication year - 1985
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.19851180932
Subject(s) - chemistry , alicyclic compound , piperidine , cationic polymerization , aqueous solution , molecule , stereochemistry , medicinal chemistry , organic chemistry
As water‐soluble macrocyclic host for apolar guest molecules, the tetraoxa[7.1.7.1]paracyclophane 1 was synthesized. In the key reaction of the synthesis, two equivalents of 1‐acetyl‐4,4‐bis(4‐hydroxy‐3,5‐dimethylphenyl)piperidine ( 4 ) and two equivalents of 1‐acetyl‐4,4‐bis[2‐( p ‐tolylsulfonyl)ethyl]piperidine ( 8 ) were cyclized to the tetraoxa[7.1.7.1]paracyclophane 9 . The synthesis of 8 starting from 1‐acetyl‐4‐piperidone is described. 1 was obtained following the reaction sequence 9 → 10 → 11 → 2 → 1 . The temperature dependency of the 1 H NMR spectra of 1 is discussed. – 1 H NMR studies of host‐guest interactions in aqueous solutions between 1 and aromatic guest molecules bearing cationic residues and between 1 and alicyclic guest molecules are described. The association constants K a (1 · mol −1 ) of the complexes were either determined by solid‐liquid extraction and from competitive inhibition experiments, or estimated from NMR complexation shifts Δδ.