Sinteza i spektroskopska karakterizacija Schiffovih baza N-supstituiranih benzimidazola kao potencijalnih senzora za metalne katione i pH u otopinama

undergraduate thesis

• Title (english): Synthesis and spectroscopic characterization of N-substituted benzimidazole Schiff bases as potential sensors for metal cations and pH in solutions
• Author: Marijana Buljubašić
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Petar Kassal (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2020-09-23, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza i spektroskopska karakterizacija Schiffovih baza N-supstituiranih benzimidazola. Ciljani spojevi su priređeni klasičnim metodama organske sinteze te nekataliziranom aminacijom potpomognutnom mikrovalnim zračenjem. Derivat 3-nitro-4-(N-fenilamino)benzonitril 3 priređen je reakcijom nukleofilne aromatske supstitucije potpomognute mikrovalovima iz 4-klor-3-nitrobenzonitrila 1. Reakcijom redukcije spoja 3 priređen je amino supstituirani derivat 3-amino-4-(N-fenilamino)benzonitril 5. Reakcijom kondenzacije spojeva 5 i 6 s BrCN otopljenim u acetonitrilu i metanolu priređeni su spojevi 8 i 9. Kondenzacijom 8 i 9 s 4-N,N-dietilamino-2-hidroksibenzaldehidom 7 priređen je ciljani derivat Schiffove baze 10, a ciljani spoj 11 je neuspješno izoliran. Struktura svih priređenih spojeva potvrđena je korištenjem 1H i 13C NMR spektroskopije. Ciljani spoj 10 je okarakteriziran UV/Vid spektroskopijom u nekoliko otapala različite polarnosti. Kako bi se ispitala njegova moguća primjena kao senzora za detekciju pH, provedene su UV/Vid titracije otopine spoja s otopinama pufera različitog pH.

Abstract (english)

The aim of this study was the synthesis and spectroscopic characterization of N-benzimidazole derived Schiff bases. Targeted compounds were prepared by classical reactions of organic chemistry and uncatalyzed microwave assisted amination.
3-nitro-4-(N-phenylamino)benzonitrile 3 was prepared by microwave assisted reaction of nucleophilic aromatic substitution from 4-chloro-3-nitrobenzonitrile 1. By reduction of compound 3, anamino-substituted derivate of 3-amino-4-(N-phenylamino)benzonitrile 5 was prepared. Compounds 8 and 9 were prepared by the condensation reaction of compounds 5 and 6 using BrCN dissolved in acetonitrile and methanol. In the reaction of compounds 8 and 9 with 4-N,N-diethylamino-2-hydroxybenzaldehyde 7, thetargeted Schiff base 10 was prepared, while compound 11 was not isolated. The structure of all synthesized compounds were confirmed by means of 1H and 13C NMR spectroscopy. Targeted compound 10 was characterized by UV/Vis spectroscopy in several organic solvents having different polarity. In order to explore the possible application of compound 10 as sensor for detection pH, UV/Vis titration of aqueous compound solution with buffer solutions with different pH were performed.

• Keywords: Schiffove baze; benzimidazoli; UV/Vid i NMR spektroskopija; pH senzori
• Keywords (english): Schiff bases; benzimidazoles; UV/Vis and NMR spectroscopy; pH sensors
• Language: croatian
• URN:NBN: urn:nbn:hr:149:128998
• Project: Number: IP-2018-01-4379; Title: Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa; Acronym: AntioxPot; Leader: Marijana Hranjec; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Chemical Engineering - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2023-05-03 10:07:09