Towards the Discrimination of Carboxylates by Hydrogen-Bond Donor Anion Receptors

The binding constants (log Kass) of small synthetic receptor molecules based on indolocarbazole, carbazole, indole, urea and some others, as well as their combinations were measured for small carboxylate anions of different basicity, hydrophilicity and steric demands, that is, trimethylacetate, acet...

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Bibliographic Details
Published in:Chemistry : a European journal 2015-03, Vol.21 (13), p.5145-5160
Main Authors: Kadam, Sandip A., Martin, Kerli, Haav, Kristjan, Toom, Lauri, Mayeux, Charly, Pung, Astrid, Gale, Philip A., Hiscock, Jennifer R., Brooks, Simon J., Kirby, Isabelle L., Busschaert, Nathalie, Leito, Ivo
Format: Article
Language:English
Subjects:
Anions
Basicity
Binding
Bond strength
carboxylate anions
Carboxylates
Chemistry
Discrimination
Hydrophilicity
hydrophobic effects
Ions
molecular recognition
NMR spectroscopy
Receptors
Strength
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Summary:The binding constants (log Kass) of small synthetic receptor molecules based on indolocarbazole, carbazole, indole, urea and some others, as well as their combinations were measured for small carboxylate anions of different basicity, hydrophilicity and steric demands, that is, trimethylacetate, acetate, benzoate and lactate, in 0.5 % H2O/[D6]DMSO by using the relative NMR‐based measurement method. As a result, four separate binding affinity scales (ladders) including thirty‐eight receptors were obtained with the scales anchored to indolocarbazole. The results indicate that the binding strength is largely, but not fully, determined by the strength of the primary hydrogen‐bonding interaction. The latter in turn is largely determined by the basicity of the anion. The higher is the basicity of the anion the stronger in general is the binding, leading to the approximate order of increasing binding strength, lactate
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201405858