Synthesis and ESI-MS Alkali Metal Ion Binding Selectivities of Cone, Partial Cone, and 1,3-Alternate 1,3-Bis(α-picolyloxy)-p-tert-butylcalix[4]arene Crown-6 and 1,1'-Binaphthalene-2,2'-diyl Crown-6 Conformers

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Title:Synthesis and ESI-MS Alkali Metal Ion Binding Selectivities of Cone, Partial Cone, and 1,3-Alternate 1,3-Bis(α-picolyloxy)-p-tert-butylcalix[4]arene Crown-6 and 1,1'-Binaphthalene-2,2'-diyl Crown-6 Conformers
Creators:
Ferguson, George
Lough, Alan J.
Notti, Anna
Pappalardo, Sebastiano
Parisi, Melchiorre F.
Resnati, Giuseppe
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 5, pp. 1109-1125
Uncontrolled Keywords:Pyridine derivatives, Calixarenes, X-Ray diffraction, Crown compounds, Electrospray ionization mass spectrometry, Biaryls, Alkali metal ion selectivity, Binaphthalenes

Abstract

The syntheses of 1,3-bis(α-picolyloxy)-<i>p-tert</i>-butylcalix[4]arene crown-6 and 1,1'-binaphthalene-2,2'-diyl crown-6 title conformers have been achieved by two complementary synthetic strategies, which differ in the order in which the polyether loop and the pendant picolyl groups are introduced. The structure and conformation of all new compounds have been firmly established by NMR spectroscopy, and further proven by X-ray analysis for the intermediate <i>p-tert</i>-butyl-25,27-(1,1'-binaphthalene-2,2'-diyl-crown-6)-26,28-dihydroxycalix[4]arene. Within each set of conformers, the nature of the polyether chain has little or no influence on the overall conformation of the calixarene platform. The alkali metal ion binding selectivities of the two series of calixarenes have been evaluated in competitive complexation experiments by electrospray ionization mass spectrometry. In the <i>p-tert</i>-butylcalix[4]arene crown-6 series, partial cone and 1,3-alternate conformers show a peak selectivity for the larger Cs<sup>+</sup> ions, while the cone one preferentially binds the smaller Na<sup>+</sup> ions. On the other hand, the cone and 1,3-alternate binaphthyl-containing analogues show a preference for Na<sup>+</sup> ions, the partial cone being quite unselective. <p>

Title:Synthesis and ESI-MS Alkali Metal Ion Binding Selectivities of Cone, Partial Cone, and 1,3-Alternate 1,3-Bis(α-picolyloxy)-p-tert-butylcalix[4]arene Crown-6 and 1,1'-Binaphthalene-2,2'-diyl Crown-6 Conformers
Creators:
Ferguson, George
Lough, Alan J.
Notti, Anna
Pappalardo, Sebastiano
Parisi, Melchiorre F.
Resnati, Giuseppe
Uncontrolled Keywords:Pyridine derivatives, Calixarenes, X-Ray diffraction, Crown compounds, Electrospray ionization mass spectrometry, Biaryls, Alkali metal ion selectivity, Binaphthalenes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:5
Page Range:pp. 1109-1125
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041109UNSPECIFIED
ID Code:2264
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Ferguson, George; Lough, Alan J.; Notti, Anna; Pappalardo, Sebastiano; Parisi, Melchiorre F.; Resnati, Giuseppe (2004) Synthesis and ESI-MS Alkali Metal Ion Binding Selectivities of Cone, Partial Cone, and 1,3-Alternate 1,3-Bis(α-picolyloxy)-p-tert-butylcalix[4]arene Crown-6 and 1,1'-Binaphthalene-2,2'-diyl Crown-6 Conformers. Collection of Czechoslovak Chemical Communications, 69 (5). pp. 1109-1125. ISSN 0010-0765

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