Related Experiment Video
Updated: Aug 16, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Thiourea-Functionalized Glycophane Macrocycles for Selective Recognition of Phthalate Isomers
Fernando Ortega-Caballero1,2, Carmen Ortiz Mellet1, José Manuel García Fernández3
1Department of Organic Chemistry, Faculty of Chemistry, University of Seville, c/Profesor García González 1, Sevilla41012, Spain.
Abstract:
We report the synthesis of water-soluble glycophanes tailored for the selective recognition of related aromatic dicarboxylic acids─phthalate isomers─in both DMSO-d6 and highly competitive D2O. Key novel design aspects are the generation of distal thiourea hydrogen bonding donors by isothiocyanate-amino coupling of C2-symmetric aryl pseudodisaccharides or the stepwise elaboration of α,α'-d-trehalose scaffolds. NMR titrations revealed differentiated binding constants across host-guest pairs, including the water recognition of sodium terephthalate.

