The crystal landscape and cocrystallization of primary aromatic sulfonamides

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Downey, John D.
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University College Cork
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This thesis is focused on primary benzenesulfonamides. They have been structurally characterised and analysed for common structural motifs present in the solid state. A systematic investigation of their cocrystallization with a range of neutral, zwitterionic and ionic coformers has been carried, with a strong focus on coformers that have the potential for sulfonamide drug development. Chapter One discusses and illustrates the literature for the solid-state and supramolecular chemistry of benzenesulfonamides; topics covered include non-covalent interactions, synthons, crystal engineering, cocrystallization, eutectic compositions, solvates, biochemistry of sulfa drugs and crystal polymorphism. Chapter Two delves into the crystal landscape of the sulfonamide functional group. In this chapter we critically assess several simple primary aromatic sulfonamides identifying the different motifs present in their crystalline structures. Chapter Three focuses on the design and cocrystallization of sulfonamides with a range of neutral, zwitterion and ionic coformers. Initial screening was complemented by the solid-state characterization of the products obtained. Chapter Four outlines the future work that could be implemented to advance the library of supramolecular synthons for the sulfonamide functional group, in addition to furthering the improvement of sulfonamide drug development whether by using cocrystallization, solvate formation or by eutectic compositions.
Cocrystal , Sulfonamide , Crystal landscape
Downey, J. D. 2020. The crystal landscape and cocrystallization of primary aromatic sulfonamides. MRes Thesis, University College Cork.
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