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    Multi-component crystals of 4-phenylpyridine: challenging the boundaries between co-crystal and organic salt formation with insight into solid-state proton transfer

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    Publication date
    2013
    Author
    Seaton, Colin C.
    Munshi, Tasnim
    Williams, Sara E.
    Scowen, Ian J.
    Keyword
    REF 2014; Multi-component crystals; 4-phenylpyridine; Benzoic acids; Co-crystal formation; Organic salt formation; Proton transfer
    
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    Abstract
    Six new multi-component crystals between 4-phenylpyridine and substituted benzoic acids (3-nitrobenzoic acid, 3,5-dinitrobenzoic acid, gallic acid, 4-aminobenozic acid, salicylic acid and 2-aminobenzoic acid) were created and characterized crystallographically to investigate the influence of chemical and structural factors on the hydrogen location between the two components. While the expected intermolecular interactions are formed between the acid and pyridine group in most cases, the gallic acid structure is anomalous forming an unexpected salt with pyridine to hydroxyl interactions. Calculations of the hydrogen bonding motifs indicate that the level of proton transfer (e.g. salt versus co-crystal formation) is not solely a function of the dimer geometry but influenced by the local crystallographic environment. Analysis of the crystal structures indicates the strength of the hydrogen bonding into this motif alters the expected protonation state from chemical considerations.
    URI
    http://hdl.handle.net/10454/6176
    Citation
    Seaton, C. C., Munshi, Tasnim, Williams, Sara E., Scowen, Ian J. (2013b) Multi-component crystals of 4-phenylpyridine: challenging the boundaries between co-crystal and organic salt formation with insight into solid-state proton transfer. CrystEngComm, 15(26), 5250-5260.
    Link to publisher’s version
    http://dx.doi.org/10.1039/c3ce40499d
    Type
    Article
    Collections
    Life Sciences Publications

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