Synthesis and anion recognition studies of new oligomethylene bis(nitrophenylureylbenzamide) receptors

José García-Elías, Adrián Ochoa-Terán*, Anatoli K. Yatsimirsky, Hisila Santacruz Ortega, Karen Ochoa-Lara, Luis Miguel López-Martínez, Christian L. Castro-Riquelme, Ángel L. García, Domingo Madrigal-Peralta, Victoria Labastida-Galván, Mario Ordoñez

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A new series of oligomethylene bis(nitrophenylureylbenzamide) receptors were synthesized varying the relative position of the urea and amide groups (ortho4 and meta8) and the length of the oligomethylene chain (C2 to C8). An anion recognition study was performed with TBAX salts (X = AcO-, BzO-, F-, H2PO4-, and HP2O73-) by UV-vis and 1H NMR. The flexibility of these receptors allows a cooperative effect of both ureylbenzamide units in the receptors. Noteworthy, the ortho position favored the 1 : 1 stoichiometry in the complexes with the carboxylates. The formation of 2 : 1 receptor-anion complexes with both types of receptors 4 and 8 and with hydrogen pyrophosphate and high log K values obtained were very significant in this work. The NMR studies evidenced the formation of supramolecular complexes, even in a competitive solvent, such as DMSO.

Original languageEnglish
Pages (from-to)39147-39162
Number of pages16
JournalRSC Advances
Volume9
Issue number67
DOIs
StatePublished - 2019

Bibliographical note

Publisher Copyright:
© 2019 The Royal Society of Chemistry.

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