Sinteza novih ferocen-piridinskih liganada i odabranih metalnih kompleksa

undergraduate thesis

• Title (english): Synthesis of new ferrocene-pyridine ligands and their metal complexes
• Author: Lucija Piškur
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Dajana Kučić Grgić (član povjerenstva)
• Committee member: Ida Boček Pavlinac (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2023-09-21, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovog rada bila je sinteza novih ferocen-piridinskih liganada (6–9) i njihovih
Re(I)-(6-Re–8-Re) i Ru(II)-kompleksa (6-Ru-cim–9-Ru-cim, 8-Ru–fenil). Ligandi su sintetizirani regioselektivnom 1,3-dipolarnom cikloadicijom iz prethodno sintetiziranih terminalnih ferocenskih alkina (3–5) i kloriranog piridin-2-aldoksima (2). Terminalni ferocenski alkini (3–5) sintetizirani su O-propargiliranjem ferocen alkohola, ferocen aldoksima i ferocen karboksilne kiseline s propargil-bromidom uz prisutstvo baze. Klorirani aldoksimski
prekursor (2) sintetiziran je iz piridin-2-aldehida u dva stupnja. U prvom je stupnju
piridin-karbaldehid preveden u piridin-aldoksim (1), koji je u drugom stupnju kloriran s N-klorsukcinimidom. Sintetizirani piridin-izoksazoli (6–9) korišteni su kao ligandi za metalne komplekse s renij(I) pentakarbonil-kloridom (6-Re–8-Re), diklor(benzen)rutenij(II) dimerom (8-Ru–fenil) i diklor(p-cimen)rutenij(II) dimerom (6-Ru-cim–9-Ru-cim). Strukture spojeva potvrđene su spektroskopijom 1H i 13C NMR.

Abstract (english)

The aim of this work was the synthesis of new ferrocene-pyridine ligands (6–9) and their Re(I)-(6-Re–8-Re) and Ru(II)-complexes (6-Ru-cym–9-Ru-cym, 8-Ru-phenyl). Ligands were synthesized by regioselective 1,3-dipolar cycloaddition from previously synthesized terminal ferrocene alkynes (3–5) and chlorinated pyridine-2-aldoxime (2). Terminal ferrocene alkynes (3–5) were synthesized by O-propargylation of ferrocene alcohol, ferrocene aldoxime and ferrocene carboxylic acid with propargyl bromide in the presence of a base. The chlorinated aldoxime precursor (2) was synthesized from pyridine-2-carbaldehyde in two steps. In the first step, pyridine carbaldehyde was converted into pyridine aldoxime (1), which was chlorinated with N-chlorosuccinimide in the second step. Synthesized pyridine isoxazoles (6–9) were used as ligands for metal complexes with rhenium(I) pentacarbonyl chloride, dichloro(benzene)ruthenium(II) dimer and dichloro(p-cymene)ruthenium(II) dimer.
The structures of the compounds were confirmed by 1H and 13C NMR spectroscopy.

• Keywords: ferocen; izoksazol; metalni kompleksi; renij; rutenij
• Keywords (english): ferrocene; isoxazole; metal complexes; rhenium; ruthenium
• Language: croatian
• URN:NBN: urn:nbn:hr:149:348783
• Project: Number: IP-2018-01-4682; Title: Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja; Acronym: PurBioCaPa; Leader: Silvana Raić-Malić; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2026-09-01
• Created on: 2023-11-30 09:43:11