Synthesis and anion binding properties of a urea-based molecular cleft

Ismet Basaran,Xi Wang,Azmain Alamgir,Jing Wang,Syed A Haque,Yazhou Zhang,Douglas R Powell,Jerzy Leszczynski,Md Alamgir Hossain

doi:10.1016/j.tetlet.2014.12.015

Synthesis and anion binding properties of a urea-based molecular cleft

Ismet Basaran, Xi Wang + Show 7 more

https://doi.org/10.1016/j.tetlet.2014.12.015

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Journal: Tetrahedron Letters	Publication Date: Dec 19, 2014
Citations: 16

Affiliation: Jackson State University, Balıkesir University, University of Oklahoma

#Binding Affinities For Anions #Density Functional Theory + Show 8 more

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Abstract

A new urea-based molecular cleft (L) derived from propylene-linked dipodal amine has been synthesized and its binding affinities for anions have been investigated by 1H NMR and UV–vis spectroscopic titrations in DMSO. The receptor has been shown to bind F−, HSO4−, H2PO4−, and AcO− in a 1:1 binding mode via hydrogen bonding interactions, providing the highest binding constant for F−. In addition, the new cleft shows a naked-eye color change in the presence of F− in DMSO. The interactions of L with fluoride have also been evaluated by theoretical calculations based on density functional theory (DFT), revealing that the cleft encapsulates a fluoride via four NH⋯F− and two CH⋯F− bonds.

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