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. 2020 May 12;25(10):2275.
doi: 10.3390/molecules25102275.

Experimental Comparative Study of Dynamic Behavior in Solution Phase of C-Tetra(phenyl)resorcin[4]arene and C-Tetra(phenyl)pyrogallol[4]arene

José Luis Casas-Hinestroza  1 , Miguel Ángel Vela Suazo  1 , Mauricio Maldonado Villamil  1
Affiliations

Experimental Comparative Study of Dynamic Behavior in Solution Phase of C-Tetra(phenyl)resorcin[4]arene and C-Tetra(phenyl)pyrogallol[4]arene

José Luis Casas-Hinestroza et al. Molecules. .

Abstract

The synthesis of phenyl-resorcinarenes and pyrogallolarenes is known to produce a conformational mixture of cone and chair isomers. Depending on the synthesis conditions the composition of the conformational mixture is variable; however, the cone conformer is the greatest proportion of phenyl-resorcin[4]arenes and chair conformer of pyrogallol[4]arenes. The experimental evidence suggests that phenyl-substituted resorcinarene and pyrogallolarene exist as a dynamic boat in solution.

Keywords: conformational behavior; conformers; dynamic boat; dynamic studies; polyhydroxylated platform.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of resorcinarenes and pyrogallolarenes.
Scheme 2
Scheme 2
Synthesis of tetra(phenyl) pyrogallol[4]arene and resocin[4]arene.
Figure 1
Figure 1
Comparative 1H-NMR spectra of de products 2a and 2b in DMSO-d6 at room temperature.
Figure 2
Figure 2
Dynamic study of tetra(phenyl)-resorcin[4]arene (1a) in MeCN-DMSO-d6 mixture.
Figure 3
Figure 3
Dynamic behavior of 1a and 2a.
Figure 4
Figure 4
Dynamic study of tetra(phenyl)-pyrogallol[4]arene (2a) in MeCN-DMSO-d6 mixture.
See this image and copyright information in PMC

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