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    H-bond donor parameters for cations

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    Publication date
    2019
    Author
    Pike, Sarah J.
    Lavagnini, E.
    Varley, L.M.
    Cook, J.L.
    Hunter, C.A.
    Keyword
    H-bonds
    Cations
    Rights
    © 2019 Royal Society of Chemistry. This work is licensed under a Creative Commons Attribution 4.0 International License. http://creativecommons.org/licenses/by/4.0/
    Peer-Reviewed
    Yes
    
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    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 parameters for alkali metal cations decrease down the group from 5.0 (Li+) to 3.5 (Cs+).
    URI
    http://hdl.handle.net/10454/17670
    Version
    Published version
    Citation
    Pike SJ, Lavagnini E, Varley LM et al(2019) H-bond donor parameters for cations. Chemical Science. 10: 5943-5951.
    Link to publisher’s version
    https://doi.org/10.1039/C9SC00721K
    Type
    Article
    Collections
    Life Sciences Publications

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