Ferocenski kopulati 2-tiouracila: priprava i spektralna karakterizacija

master's thesis

• Title (english): Conjugates of ferrocene and 2-thiouracil: synthesis and spectral characterization
• Author: Rebeka Perčić
• Mentor: Jasmina Lapić (mentor)
• Mentor: Senka Djaković (pomoć pri izradi, neposredni voditelj)
• Committee member: Senka Djaković (predsjednik povjerenstva)
• Committee member: Valerije Vrček (član povjerenstva)
• Committee member: Antonela Ninčević Grassino (član povjerenstva)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Organic Chemistry); Zagreb
• Defense date and country: 2023-03-24, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Food Technology

Abstract

Organometalni derivati nukleobaza (OrDeN-i), nova su generacija konjugata u kojima su metaloceni povezani s temeljnim strukturnim elementima nasljeđivanja. Zbog elektrofornih i bioaktivnih svojstava, OrDeN-i nalaze primjenu u (bio)analitičkoj i medicinskoj kemiji. Ovaj diplomski rad odnosi se na pripravu kopulata ferocena i 2-tiouracila te njegovih C6 supstituiranih derivata. Ferocenoilirajući agens u ovim kopulacijama je ferocenoil klorid. Kao deprotonirajuća baza koristi se natrijev hidrid ili trietilamin, a kao otapalo koristi se acetonitril ili dioksan. U reakcijama provedenim s 2-tiouracilom u svim reakcijskim uvjetima nastaju, uz dva monoderivata N1- i N3-izomer, i dva bisderivata, N1/N3- i S/N3-izomer. U reakciji sa 6-supstituiranim 2-tiouracilom uz monoderivate nastaje isključivo samo jedan bisderivat S/N3-izomer što ukazuje da supstituent na položaju 6 baze utječe na regioselektivnost reakcije.

Abstract (english)

Organometallic nucleobases derivatives (OrDeNs) are a new generation of conjugates in which metallocenes are bonded with fundamental structural genetic elements. Due to their electrophoric and bioactive characteristics, OrDeNs are usually used in (bio)analitical and medicinal chemistry. In this graduate thesis, conjugates of ferrocene and 2-thiouracil, and also his C-6 supstituted derivatives, are synthesised. Ferrocenoylating agens used in this experiment is ferrocenoyl-chloride. Sodium hydroxide or tryethilamine are used as deprotonating bases, and acetonitrile or dioxane are used as solvents. Products of 2-thiouracil reaction, in all conditions, are two monoderivatives, N1- and N3-isomers, and two bis derivatives, N1/N3- and S/N3-isomers. On the other hand, products of 6- supstituted 2-thiouracil reactions are monoderivatives and a single bis derivative S/N3-isomer which indicates that supstituent at position 6 of 2-thiouracil impacts the regioselectivity of the reaction.

• Keywords: organometalni derivati nukleobaza; 2-tiouracil; ferocen; spektralna analiza
• Keywords (english): organometallic nucleobases derivatives; 2-thiouracil; ferrocene; spectral analysis
• Language: croatian
• URN:NBN: urn:nbn:hr:159:723447
• Study programme: Title: Food Engineering; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka prehrambenog inženjerstva (magistar/magistra inženjer/inženjerka prehrambenog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-05-21 08:19:13