Multi-point interaction-based recognition of fluoride ions by tert -butyldihomooxacalix[4]arenes bearing phenolic hydroxyls and thiourea

A series of p-tert -butyldihomooxacalix[4]arenes bearing phenolic hydroxyls and thiourea moieties were prepared to investigate their anion binding behavior. These compounds showed F − binding according to 1 H NMR titration experiments. Among them, dihomooxacalix[4]arenes bearing phenyl and benzyl th...

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Bibliographic Details
Published in:New journal of chemistry 2019, Vol.43 (14), p.5503-5511
Main Authors: Zhao, Ling-Ling, Yang, Xiao-Song, Chong, Hui, Wang, Yang, Yan, Chao-Guo
Format: Article
Language:English
Subjects:
Aromatic compounds
Bearing
Binding
Chemical equilibrium
Hydrogen bonds
NMR spectroscopy
Organic chemistry
Spectrum analysis
Thioureas
Titration
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Summary:A series of p-tert -butyldihomooxacalix[4]arenes bearing phenolic hydroxyls and thiourea moieties were prepared to investigate their anion binding behavior. These compounds showed F − binding according to 1 H NMR titration experiments. Among them, dihomooxacalix[4]arenes bearing phenyl and benzyl thiourea ( 2a and 2b ) showed multiple interactions with added F − , including N–H⋯F, O–H⋯F hydrogen bonds and “through-space” C–H⋯F − interactions between F − and the attached aromatic segment of thiourea. A conformational change of the dihomooxacalix[4]arene cavity was observed as well and proved by theoretical calculations. The dihomooxacalix[4]arene bearing methyl thiourea ( 2c ) also showed the formation of N–H⋯F, O–H⋯F hydrogen bonds, but less conformational change of the dihomooxacalix[4]arene cavity according to 1 H NMR titration results. The bis-dihomooxacalix[4]arene ( 3 ) showed clear N–H⋯F hydrogen bond formation upon addition of F − as characterized by 1 H NMR spectroscopy.
ISSN:1144-0546
1369-9261
DOI:10.1039/C8NJ06333H