The synthesis and chemistry of Quinolino(7,8-h)quinoline derivatives : a thesis presented in partial fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry at Massey University, Manawatu, New Zealand

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Massey University
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Proton sponges are a class of neutral organic superbases. Quinolino[7,8-h]quinoline (QQ) is one such molecule. Structurally it has two closely positioned nitrogen atoms which cause a destabilising lone electron overlap which manifests as a helical torsional twist that can be relieved by monoprotonation or complexation. These compounds are highly basic and are chelators that can accommodate a variety of ion sizes. Exploration of the structural properties of QQ provides an avenue for non-symmetric compound synthesis. Research interest arose in developing original synthetic pathways and exploring the chemistry of this QQ moiety, and its potential uses. This work primarily focussed on the development of methods towards new derivatives containing the QQ core structure, of which several were developed. Exploration of their properties as bases was begun in the context of both experimental measurements and theoretical calculations, allowing some to be classified as superbases. Computational analysis also gave insight into structural changes taking place during the protonation process. Potential uses of QQ derivatives as chelators for metals were examined. An X-ray crystal structure of a beryllium containing 4,9-dihydroxyquinolino[7,8-h]quinoline was achieved, the 7th reported ion to be chelated by a QQ compound.
Beryllium, Chelates, Ligands, Synthesis