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Hydrogen bonding in proton-transfer compounds of 5-sulfosalicylic acid with ortho-substituted monocyclic heteroaromatic Lewis bases

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The crystal structures of the 1:1 proton-transfer compounds of 5-sulfosalicylic acid with the ortho-substituted monocyclic heteroaromatic Lewis bases, 2-aminopyridine, 2-hydroxypyridine and 2-aminopyrimidine, viz. 2-aminopyridinium 5-sulfosalicylate (1), 2-hydroxypyridinium 5-sulfosalicylate monohydrate (2) and 2-aminopyrimidinium 5-sulfosalicylate monohydrate (3) have been determined and their hydrogen-bonding patterns described. All compounds are monoclinic, space group P21/c, with Z=4 in cells with dimensions a=7.898(5), b=11.159(11), c=14.912(7) Å, β=96.849(11)° (1);=7.260(2), b=15.292(3), c=12.615(2) Å, β=102.45(5)° (2) and a=7.0430(7), b=12.1871(16), c=16.2825(12) Å, β=101.364(7)° (3). All three compounds show some molecular disorder, in 1 within the cation species and with both 2 and 3, a similar rotational disorder in the anion sulfonate group. Hydrogen bonding in all three compounds together with significant cation-anion or cation-cation inter-ring π–π interactions generate three-dimensional layered polymer structures.

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Acknowledgments

The authors acknowledge financial support from the School of Physical and Chemical Sciences (Queensland University of Technology) and the School of Science, Griffith University.

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Authors and Affiliations

  1. School of Physical and Chemical Sciences, Queensland University of Technology, G.P.O. Box 2434, Brisbane, Qld, 4001, Australia

    Graham Smith

  2. School of Science, Griffith University, Nathan, Brisbane, Qld, 4111, Australia

    Urs D. Wermuth & Peter C. Healy

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  1. Graham Smith
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  2. Urs D. Wermuth
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  3. Peter C. Healy
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Correspondence to Graham Smith.

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Supplementary material

CCDC 286383, 286384 and 286385 contain supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/datarequest/cif by e-mailing datarequest@ccdc.cam.ac.uk, or contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ.

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Smith, G., Wermuth, U.D. & Healy, P.C. Hydrogen bonding in proton-transfer compounds of 5-sulfosalicylic acid with ortho-substituted monocyclic heteroaromatic Lewis bases. J Chem Crystallogr 36, 841–849 (2006). https://doi.org/10.1007/s10870-006-9122-4

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