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Molecules 2015, 20(6), 9915-9928; doi:10.3390/molecules20069915

Synthesis and Characterization of Two Sulfonated Resorcinarenes: A New Example of a Linear Array of Sodium Centers and Macrocycles

1
Departamento de Química, Universidad de los Andes, Cr. 1 No. 18A 10, Bogotá 111711, Colombia
2
Química Física, Universidad de Alcalá, Alcalá de Henares 28871, Spain
3
Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Alcalá de Henares 28871, Spain
4
Departamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogotá, Cr. 30 No. 45-03, Bogotá 111321, Colombia
*
Author to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 5 March 2015 / Revised: 6 May 2015 / Accepted: 7 May 2015 / Published: 28 May 2015
(This article belongs to the Section Organic Synthesis)
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Abstract

Two sulfonated resorcinarenes were synthesized by reacting C-tetra(butyl) resorcinarene or C-tetra(2-(methylthio)ethyl)resorcinarene with formaldehyde in the presence of sodium sulfite. Their structures were determined via FT-IR, 1H-NMR, 13C-NMR and mass spectrometry. Thermal gravimetric analyses of the derivatives were also carried out and revealed the presence of water molecules in the solid state. The sulfonated product of C-tetra(butyl)resorcinarene was characterized by an X-ray crystal structure determination. The asymmetric unit contains eight molecules of water and two of acetone, and analysis indicated that sulfonated resorcinarene prefers a cone configuration (rccc conformation) in the solid state. In the crystal array, classical hydrogen bond interactions O-H···O and intermolecular contacts were observed. In the crystal packing, a linear array of capsules of sulfonated resorcinarenes was generated for a chain of sodium atoms and sulfonate groups. View Full-Text
Keywords: sulfonation; water soluble resorcinarene; cone conformation sulfonation; water soluble resorcinarene; cone conformation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Sanabria, E.; Esteso, M.Á.; Pérez-Redondo, A.; Vargas, E.; Maldonado, M. Synthesis and Characterization of Two Sulfonated Resorcinarenes: A New Example of a Linear Array of Sodium Centers and Macrocycles. Molecules 2015, 20, 9915-9928.

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