Synthesis of Perfluoroaryl Heterocycles To Provide Synthons For Crystal Engineering Using π−π Stacking Interactions

Althagbi, Hanan Ibrahim

Synthesis of Perfluoroaryl Heterocycles To Provide Synthons For Crystal Engineering Using π−π Stacking Interactions

dc.contributor.advisor	Saunders, Graham C.
dc.contributor.author	Althagbi, Hanan Ibrahim
dc.date.accessioned	2014-08-01T03:43:59Z
dc.date.available	2017-02-20T02:31:50Z
dc.date.issued	2013
dc.date.updated	2013-07-18T06:42:02Z
dc.description.abstract	Approximately 42 new arene-perfluoroarene compounds were synthesised by the reaction of pentafluorophenyl derivatives (C₆F₅R; R= CN, Br, Cl, I, CHO, CF₃, H) with imidazole, benzimidazole, parazole, indazole and their derivatives such as 2-methylimidazole, 4-methylimidazole, 2-phenylimidazole and 2-methylbenz-imidazole. Attempts to synthesize 1-(2,3,5,6-tetrafluoropyridyl)pyrazole and 1-(2,3,5,6-tetrafluoropyridyl)indazole were unsuccessful. However, these reactions were achieved using different solvents, varying amounts of solvents and varying temperatures. Various chemical analytical techniques, such as NMR spectroscopy, mass spectrometry, infrared spectroscopy, single-crystal X-diffraction and micro-elemental analysis, were used to characterise the compounds. The crystallization of these compounds was performed by the slow evaporation of their solutions in different solvents at ambient temperature. Single crystal structures were obtained for 1-(2,3,5,6- tetrafluoropyridyl)-2-methylbenzimidazole, 1-(4-bromo-2,3,5,6-tetrafluorobenzyl)-3-benzyl-4-methylimidazolium bromide and 1-(2,3,5,6-tetrafluoropyridyl)-3-benzyl-4-methylimidazolium bromide and this result has shown that π-π stacking interactions have an essential role in the packing of these compounds.
dc.format.mimetype	application/pdf
dc.identifier.citation	Althagbi, H. I. (2013). Synthesis of Perfluoroaryl Heterocycles To Provide Synthons For Crystal Engineering Using π−π Stacking Interactions (Thesis, Master of Science (MSc)). University of Waikato, Hamilton, New Zealand. Retrieved from https://hdl.handle.net/10289/8732	en
dc.identifier.uri	https://hdl.handle.net/10289/8732
dc.language.iso	en
dc.publisher	University of Waikato
dc.rights	All items in Research Commons are provided for private study and research purposes and are protected by copyright with all rights reserved unless otherwise indicated.
dc.subject	synthesis of perfluoroaryl heterocycles
dc.subject	pentafluorophenyl derivatives
dc.subject	imidazole, benzimidazole, parazole, indazole and their derivatives
dc.subject	π-π stacking interactions
dc.subject	crystal engineering
dc.subject	Synthons
dc.title	Synthesis of Perfluoroaryl Heterocycles To Provide Synthons For Crystal Engineering Using π−π Stacking Interactions
dc.type	Thesis
pubs.place-of-publication	Hamilton, New Zealand	en_NZ
thesis.degree.grantor	University of Waikato
thesis.degree.level	Masters
thesis.degree.name	Master of Science (MSc)