H-Bond donor parameters for cations

Chemical Science
Sarah J PikeChristopher A Hunter

Abstract

UV/Vis absorption and NMR spectroscopy titrations have been used to investigate the formation of complexes between cations and neutral H-bond acceptors in organic solvents. Complexes formed by two different H-bond acceptors with fifteen different cations were studied in acetone and in acetonitrile. The effects of water and ion pairing with the counter-anion were found to be negligible in the two polar solvents employed for this study. The data were used to determine self-consistent H-bond donor parameters (α) for a series of organic and inorganic cations; guanidinium, primary, tertiary and quaternary ammonium, imidazolium, methylpyridinium, lithium, sodium, potassium, rubidium and caesium. The results demonstrate the transferability of α parameters for cations between different solvents and different H-bond acceptor partners, allowing reliable prediction of cation recognition properties in different environments. Lithium and protonated nitrogen cations form the most stable complexes, but the α parameter is only 5.0, which is similar to the neutral H-bond donor 3-trifluoromethyl,4-nitrophenol (α = 5.1). Quaternary ammonium is the weakest H-bond donor investigated with an α value of 2.7, which is comparable to an alcohol. The α p...Continue Reading

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Nov 7, 2017·Organic & Biomolecular Chemistry·Sarah J Pike, Christopher A Hunter

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Citations

Oct 13, 2020·Physical Chemistry Chemical Physics : PCCP·Alexandra SchindlChristof M Jäger
Mar 6, 2020·Chemical Science·Tao JiangHe Tian
Nov 26, 2019·Journal of the American Chemical Society·Andrew W WijayaRonald N Zuckermann
Sep 3, 2021·Nature·Mark P WalshMatthew O Kitching

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