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undergraduate thesis
Novi 3-tienostilbenski oksimi – sinteza i spektroskopska karakterizacija
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. urn:nbn:hr:149:294639
Ernečić, Amalija
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Ernečić, A. (2021). Novi 3-tienostilbenski oksimi – sinteza i spektroskopska karakterizacija (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:294639

Ernečić, Amalija. "Novi 3-tienostilbenski oksimi – sinteza i spektroskopska karakterizacija." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. https://urn.nsk.hr/urn:nbn:hr:149:294639

Ernečić, Amalija. "Novi 3-tienostilbenski oksimi – sinteza i spektroskopska karakterizacija." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. https://urn.nsk.hr/urn:nbn:hr:149:294639

Ernečić, A. (2021). 'Novi 3-tienostilbenski oksimi – sinteza i spektroskopska karakterizacija', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:294639

Ernečić A. Novi 3-tienostilbenski oksimi – sinteza i spektroskopska karakterizacija [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2021 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:294639

A. Ernečić, "Novi 3-tienostilbenski oksimi – sinteza i spektroskopska karakterizacija", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:149:294639

Metadata
TitleNovi 3-tienostilbenski oksimi – sinteza i spektroskopska karakterizacija
Title (english)New 3-thienostilbene oximes - synthesis and spectroscopic characterization
AuthorAmalija Ernečić
MentorIrena Škorić (mentor)
Committee memberIrena Škorić (predsjednik povjerenstva)
Committee memberDragana Vuk (član povjerenstva)
Committee memberSandra Babić (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2021-09-09, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
S ciljem pronalaska novih potencijalnih reaktivatora enzima acetilkolinesteraze inhibiranog djelovanjem organofosfornih živčanih agenasa sintetizirani su novi derivati 3-tienostilbenskih oksima. Wittigovom reakcijom sintetizirani su cis- i trans-heterostilbeni iz 3-tienilnog aldehida i p-supstituiranih fosfonijevih soli kao polazne strukture s ciljem prevođenja u oksim. Tri odabrane soli kao supstituente na benzenskom prstenu sadržavale su metilnu skupinu, klor i cijano-skupinu. Heterostilbeni su funkcionalizirani Vilsmeierovim formiliranjem čime su dobiveni karbaldehidi. Karbaldehidi su u zadnjem sintetskom koraku prevedeni u oksime reakcijom oksimiranja uz hidroksilamin hidroklorid kao reagens. Ukupno je dobiveno i izolirano dvanaest oksima od kojih su četiri oksima s metilnim supstituentom i dva oksima s cijano-supstituentom dobiveni u dovoljnoj količini za biološka istraživanja reaktivacije enzima acetilkolinesteraze. Svi međuprodukti i produkti pročišćeni su kolonskom kromatografijom, a strukture su im okarakterizirane i potvrđene 1H i 13C NMR spektrima.
Abstract (english)
In order to find new potential reactivators of the enzyme acetylcholinesterase inhibited by the organophosphorus nerve agents, new derivatives of 3-thienostilbene oximes were synthesized. Wittig reaction yielded cis and trans heterostilbene isomers that were synthesized from 3-thienyl aldehyde and p-substituted phosphonium salts as the starting structures with the aim of conversion to the oxime. The three selected salts contained methyl, chlorine and a cyano group as a supstituent on the benzene ring. Heterostilbenes were functionalized by Vilsmeier formylation to give carbaldehydes. In the last synthetic step, the carbaldehydes were converted to oximes by an oximation reaction with hydroxylamine hydrochloride as a reagent. A total of twelve oximes were obtained and isolated of which four oximes with methyl substituent and two oximes with cyano substituent were obtained in sufficient quantity for biological studies of acetylcholinesterase enzyme reactivation. All intermediates and products were purified by column chromatography and their structures were characterized and confirmed by 1H and 13C NMR spectra.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:294639
Study programmeTitle: 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 resourceText
File originBorn digital
Access conditionsOpen access
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Created on2023-03-28 07:33:18