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Synthesis and structural and spectroscopic studies of carboxyalkyl (benz)imidazole derivatives and their dimers with polymethylene linker

Łukasz Czekański

Abstract

The aim of my dissertation was the synthesis, spectroscopic and structural studies of the new derivatives of 1-methylbenzimidazole and their complexes with Cu (II) and Zn (II) metals. The imidazole ring is part of many bioactive molecules, i.e. histamine, histidine, pilocarpine, allantoin. Imidazole derivatives have found a number of uses in catalysis (in the form of ionic liquids), pharmacy or agrochemicals as herbicides. In my dissertation, as a result of quaternization of nitrogen atom of 1-methylbenzimidazole, I have obtained a series of compounds: ester, carboxy and betaine derivatives. The carboxyl and ester derivatives form Cu(II) and Zn(II) complexes, containing complexed dianions - tetrahalogenometallates. On the other hand, betaine complexes contain, in their structure, a fragment with perfectly linear Br-Cu-Br and O-Cu-O bonds. The obtained compounds constitute an interesting object of spectroscopic and structural research, due to the variety of interactions and structures. Synthesized 1-methylbenzimidazole derivatives were characterized by proton and carbon nuclear magnetic resonance (1H and 13C NMR), infrared spectroscopy (FT-IR), paramagnetic electron resonance (EPR), ultraviolet and visible spectroscopy (UV-Vis) X-ray diffraction (XRD) and elemental analysis. The compounds obtained were also tested for antifungal activity (Aspergillus nigre van Tieghem).
Record ID
UAMeeb68b96d7874e6ca2f1593cb859de37
Diploma type
Doctor of Philosophy
Author
Łukasz Czekański (SNŚ/WC/FoC) Łukasz Czekański,,
Title in Polish
Synteza oraz badania strukturalne i spektroskopowe pochodnych karboksyalkilo (benz)imidazolu oraz ich dimerów z łącznikiem polimetylowym
Title in English
Synthesis and structural and spectroscopic studies of carboxyalkyl (benz)imidazole derivatives and their dimers with polymethylene linker
Language
pl Polish
Certifying Unit
Faculty of Chemistry (SNŚ/WC/FoC)
Discipline
chemistry / (chemical sciences domain) / (physical sciences)
Scientific discipline (2.0)
6.5 chemical sciences
Defense Date
17-01-2018
End date
17-01-2018
Supervisor
URL
http://hdl.handle.net/10593/21270 opening in a new tab
Keywords in English
benzimidazole, betaine, complexes
Abstract in English
The aim of my dissertation was the synthesis, spectroscopic and structural studies of the new derivatives of 1-methylbenzimidazole and their complexes with Cu (II) and Zn (II) metals. The imidazole ring is part of many bioactive molecules, i.e. histamine, histidine, pilocarpine, allantoin. Imidazole derivatives have found a number of uses in catalysis (in the form of ionic liquids), pharmacy or agrochemicals as herbicides. In my dissertation, as a result of quaternization of nitrogen atom of 1-methylbenzimidazole, I have obtained a series of compounds: ester, carboxy and betaine derivatives. The carboxyl and ester derivatives form Cu(II) and Zn(II) complexes, containing complexed dianions - tetrahalogenometallates. On the other hand, betaine complexes contain, in their structure, a fragment with perfectly linear Br-Cu-Br and O-Cu-O bonds. The obtained compounds constitute an interesting object of spectroscopic and structural research, due to the variety of interactions and structures. Synthesized 1-methylbenzimidazole derivatives were characterized by proton and carbon nuclear magnetic resonance (1H and 13C NMR), infrared spectroscopy (FT-IR), paramagnetic electron resonance (EPR), ultraviolet and visible spectroscopy (UV-Vis) X-ray diffraction (XRD) and elemental analysis. The compounds obtained were also tested for antifungal activity (Aspergillus nigre van Tieghem).

Uniform Resource Identifier
https://researchportal.amu.edu.pl/info/phd/UAMeeb68b96d7874e6ca2f1593cb859de37/

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