Crystallographic study of sulfonamides with nitrogen-containing solvates

Bingham, Ann L (2002) Crystallographic study of sulfonamides with nitrogen-containing solvates. University of Southampton, Doctoral Thesis.

Abstract

X-ray crystal structure determinations have been made for many solvates or adducts of sulfathiazole. It was found that the most convenient way of categorising the structural data was to define two distinct sets, those with oxygen-containing functional groups and those with nitrogen-containing functional groups. Once divided, these groups became easier to divide into subsets, and patterns began to emerge. With this in mind, and given the scale of the project, it was decided to concentrate this thesis on those solvates that contain nitrogen. Where trends have been found a comparative study was executed using some of the other sulfonamides in order to discover the impetus for such patterns.

Since the crystal structures of all the compounds studied are hydrogen-bonded assemblies, a discussion of the structures of the organic solid state and the hydrogen-bonding patterns is presented.

In order to fully understand the nature of the mechanism involved in the formation of such solvates it was first necessary to assemble, collect and collate reported structural data for the known polymorphs of the sulfonamides used in this study.

The adducts of sulfathiazole were divided into two broad categories, i.e. salts and non-salts. Within these groups it was found that there is a variety of structural types. Dealing first with the non-salts there are 15 structures, all of which contain a strong amido-imido dimer. The first seven are a group of isostructural clathrates.

In section B salt structures are described. The removal of the azole proton by the guest inhibits the formation of the strong amido-imido dimer observed in section A. Here a much more varied set of structural forms were found, that have been grouped according to 'common' interactions.

In section C some of the other sulfonamide structures with dinitrile partners are presented; these were studied in order to establish some comparisons with sulfathiazole systems. All structures have been interpreted in terms of the dominant hydrogen bonding interactions and the torsion angles in the molecules.

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