Synthesis, NMR conformational analysis, complexation and transport studiesof an inherently chiral dihomooxacalix[4]arene triester

Citation
Pm. Marcos et al., Synthesis, NMR conformational analysis, complexation and transport studiesof an inherently chiral dihomooxacalix[4]arene triester, TETRAHEDRON, 57(32), 2001, pp. 6977-6984
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
32
Year of publication
2001
Pages
6977 - 6984
Database
ISI
SICI code
0040-4020(20010806)57:32<6977:SNCACA>2.0.ZU;2-N
Abstract
The synthesis of the inherently chiral triethyl ester monomethyl ether of p -tert-butyldihomooxacalix[4]arene (3) is reported. A distorted cone conform ation in solution at room temperature has been established for triester 3 b y NMR measurements (H-1, C-13, NOE 1D and 2D). The extracting and complexin g properties of 3 towards the entire alkali and alkaline earth cation serie s have been assessed by picrate extraction and stability constant determina tions. Transport experiments with metal picrates through a CH2Cl2 membrane have also been performed. Comparison is made with tetraethyl ester of p-ter t-butylcalix[4]arene (4) described in literature and also studied by us. 3 is a poor phase transfer agent and binder. In contrast, it is a good carrie r, mainly for the alkali cations and displays a selective transport for Ba2 +. (C) 2001 Elsevier Science Ltd. All rights reserved.