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

      Althagbi, Hanan Ibrahim
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      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
      Permanent Research Commons link: https://hdl.handle.net/10289/8732
      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.
      Date
      2013
      Type
      Thesis
      Degree Name
      Master of Science (MSc)
      Supervisors
      Saunders, Graham C.
      Publisher
      University of Waikato
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      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.
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