Priprave halkona i njihovih oksima

master's thesis

• Title (english): Syntheses of chalcones and their oximes
• Author: Ana Bogi
• Mentor: Ines Primožič (mentor)
• Committee member: Ines Primožič (predsjednik povjerenstva)
• Committee member: Biserka Prugovečki (član povjerenstva)
• Committee member: Sanda Rončević (član povjerenstva)
• Committee member: Ivan Kodrin (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2018-02-16, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom diplomskom radu sintetiziran je halkon te pet njegovih derivata s različitim supstituentima na različitim položajima benzenskih prstenova: 1-fenil-3-(4-dimetilaminofenil)prop-2-en-1-on, 1-fenil-3-(2,4,6-trimetilfenil)prop-2-en-1-on, 3-fenil-1-(2,4,6-trimetilfenil)prop-2-en-1-on, 1-fenil-3-(4-klorfenil)prop-2-en-1-on i 1-(2,4,6-trimetilfenil)-3-(2,4,6-trimetilfenil)prop-2-en-1-on. Spojevi su pripremljeni na dva načina: Claisen-Schimdtovom kondenzacijom u otopini uz korištenje ultrazvuka i mehanokemijskom sintezom (uz katalitički dodatak otapala). Izvedena je i sinteza oksima pripravljenih halkona, pri čemu su samo dva oksima uspješno pročišćena: 1,3-difenilprop-2-en-1-on-oksim i 1-fenil-3-(2,4,6-trimetilfenil)prop-2-en-1-on-oksim. Oksimi su pripremljeni reakcijom odgovarajućih halkona i hidroksilamonijevog klorida. Mehanokemijska sinteza oksima halkona uz dodatak različitih organskih baza (piridin, 4-dimetilaminopiridin (DMAP), 1,4-diazabiciklo[2.2.2]oktan (DABCO) te imidazol) nije se pokazala kao dobra metoda za njihovu sintezu. Pripravljenim spojevima određena su tališta te su analizirani spektroskopskim metodama: IR spektroskopijom te spektroskopijom 1H NMR i 13C NMR. Omjerom signala u 1H NMR spektrima oksima halkona određeno je da su u smjesi prisutni E- i Z-izomeri.

Abstract (english)

In this diploma thesis, chalcone and five of its derivatives with different substituents at different positions of benzene rings were obtained: 3-(4-dimethylaminophenyl)-1-phenylprop-2-en-1-one, 3-(2,4,6-trimethylphenyl)-1-phenylprop-2-en-1-one, 1-(2,4,6-trimethylphenyl)-3-phenylprop-2-en-1-one, 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one and 1-(2,4,6-trimethylphenyl)-3-(2,4,6-trimethylphenyl)prop-2-en-1-one. The compounds were prepared in two ways: Claisen-Schimdt condensation in solution using ultrasounic waves and mechanochemical synthesis (with catalytic solvent addition). The synthesis of oximes of prepared chalcones has been carried out, with only two oximes successfully purified: 1,3-diphenylprop-2-en-1-one oxime and 3-(2,4,6-trimethylphenyl)-1-phenylprop-2-en-1-one oxime. The compounds were prepared by reaction of the corresponding chalcones and hydroxylammonium chloride. Mechanochemical synthesis chalcone oxime with the addition of various organic bases (pyridine, imidazole, 4-dimethylaminopyridine (DMAP) and 1,4-diazobicyclo[2.2.2]octane (DABCO)) did not prove to be a good method for their synthesis. Melting point of synthetised compounds were determined and they were analyzed by spectroscopic methods: IR spectroscopy and 1H NMR and 13C NMR spectroscopy. Signal ratio of chalcones oximes in 1H NMR spectra determined that E and Z isomers were present in the mixture.

• Keywords: Claisen-Schimdtova kondenzacija; halkon; mehanokemijska sinteza; nukleofilna supstitucija na karbonilnom spoju; oksim halkona.
• Keywords (english): chalcone; chalcone oxime; Claisen-Schmidt condensation; mechanochemical synthesis; nucleophilic substitution at the carbonyl gruop.
• Language: croatian
• URN:NBN: urn:nbn:hr:217:568803
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2020-02-16
• Created on: 2018-02-26 16:21:29