Chelate effects in sulfate binding by amide/urea-based ligands

The influence of chelate and mini-chelate effects on sulfate binding was explored for six amide-, amide/amine-, urea-, and urea/amine-based ligands. Two of the urea-based hosts were selective for SO4(2-) in water-mixed DMSO-d6 systems. Results indicated that the mini-chelate effect provided by a sin...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2015-07, Vol.13 (25), p.6953-6957
Main Authors: Jia, Chuandong, Wang, Qi-Qiang, Begum, Rowshan Ara, Day, Victor W, Bowman-James, Kristin
Format: Article
Language:English
Subjects:
Amides - chemistry
Binding Sites
Chelating Agents - chemistry
Dimethyl Sulfoxide - chemistry
Ligands
Models, Molecular
Quaternary Ammonium Compounds - chemistry
Sulfates - chemistry
Urea - analogs & derivatives
Water - chemistry
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Summary:The influence of chelate and mini-chelate effects on sulfate binding was explored for six amide-, amide/amine-, urea-, and urea/amine-based ligands. Two of the urea-based hosts were selective for SO4(2-) in water-mixed DMSO-d6 systems. Results indicated that the mini-chelate effect provided by a single urea group with two NH binding sites appears to provide enhanced binding over two amide groups. Furthermore, additional urea binding sites incorporated into the host framework appeared to overcome to some extent competing hydration effects with increasing water content.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00618j