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Issue 12, 2021
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Simple acyclic molecules containing a single charge-assisted O–H group can recognize anions in acetonitrile : water mixtures

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Abstract

Hydroxypyridinium and hydroxyquinolinium compounds containing acidic O–H groups attached to a cationic aromatic scaffold were synthesized, i.e. N-methyl-3-hydroxypyridinium (1+) and N-methyl-8-hydroxyquinolinium (2+). These very simple compounds are capable of binding to chloride very strongly in CD3CN and with moderate strength in 9 : 1 CD3CN : D2O. Comparison with known association constants reveals that 1+ and 2+ bind chloride in CD3CN or CD3CN : D2O with comparable affinities to receptors containing significantly more hydrogen bond donors and/or higher positive charges. Crystal structures of both compounds with coordinating anions were obtained, and feature short O–H⋯anion hydrogen bonds. A receptor containing two hydroxyquinolinium groups was also prepared. While the low solubility of this compound caused difficulties, we were able to demonstrate chloride binding in a competitive 1 : 1 CD3CN : CD3OD solvent mixture. Addition of sulfate to this compound results in the formation of a crystallographically-characterised solid state anion coordination polymer.

Graphical abstract: Simple acyclic molecules containing a single charge-assisted O–H group can recognize anions in acetonitrile : water mixtures

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Article information


Submitted
15 Feb 2021
Accepted
08 Mar 2021
First published
15 Mar 2021

Org. Biomol. Chem., 2021,19, 2794-2803
Article type
Paper

Simple acyclic molecules containing a single charge-assisted O–H group can recognize anions in acetonitrile : water mixtures

R. J. Goodwin, M. T. Blyth, A. K. K. Fung, L. M. Smith, P. L. Norcott, S. Tanovic, M. L. Coote and N. G. White, Org. Biomol. Chem., 2021, 19, 2794
DOI: 10.1039/D1OB00282A

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