Synthesis,characterization, and X-ray structure of 1,2-bis-crown-5-calix[4]arene. Modeling of metal complexation |
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| Authors: | Zouhair Asfari Jean-Pierre Astier Christophe Bressot Jacques Estienne Gerard Pepe Jacques Vicens |
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| Affiliation: | (1) E.H.I.C.S., URA 405 du C.N.R.S., 1 rue Blaise Pascal, F-67008 Strasbourg, France;(2) C.R.M.C.2-C.N.R.S., Campus de Luminy, Case 913, F-13288 Marseille, France;(3) Centre Saint Jérôme, Laboratoire de Spectrométries et Dynamique Moléculaire, Case 542, Université de Provence, F-13397 Marseille, France |
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| Abstract: | 1,2-bis-crown-5-calix[4]arene (3) was prepared by reacting calix[4]arene (1) with tetraethylene glycol di-p-toluenesulphonate (2) in the presence of cesium carbonate in 9% yield. The X-ray structure of (3) was determined. Crystal data for C44H52O10 are as follows: monoclinic, space groupP2/c witha=18.006(8) Å,b=10.680(4) Å,c=22.359(6) Å,  =112.93(3)°,V=3958(6) Å3,Z=4,Dcalc=1.2 g cm–3, the finalR value is 0.11 for the 1851 observed reflections (I>3 (I)). The single crystal included two similar but slightly different molecules immobilized in a pinched-cone conformation withC2 symmetry. The two enantiomorphous molecules were analyzed by molecular mechanics using the GenMol program to model the selective alkali-metal complexation.This paper is dedicated to the commemorative issue on the 50th anniversary of calixarenes. |
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| Keywords: | Doubly crowned calix[4]arene X-ray structure proximal functionalization alkali cations modeling by molecular mechanics |
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