Termičke transformacije novih tiofenskih o-distirilbenzena

undergraduate thesis

• Title (english): Thermal transformations of novel thiophene o-distyrylbenzenes
• Author: Josipa Kolar
• Mentor: Dragana Vuk (mentor)
• Committee member: Dragana Vuk (predsjednik povjerenstva)
• Committee member: Irena Škorić (član povjerenstva)
• Committee member: Ines Despotović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2022-09-15, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovog rada je provesti kvantno-kemijski proračun te objasniti mehanizam termičke reakcije. U tu svrhu sintetiziran je 2-metil-3-tiofenski derivat o-distrilbenzena 2 uz pomoć Wittigove reakcije. Wittigova reakcija provela se pomoću difosfonijeve soli α,α'-o-ksilendibromida i 2-metil-3-tiofen-karbaldehida 1. Sinteza 2-metil-3-tiofen-karbaldehida provedena je uz pomoć N,N,N-trimetiletilendiamina, n-butillitija te smjese n-butillitija i litijevog diisopropilamida. Sintetizirani spoj 2 podvrgnut je termičkoj reakciji u kiselom mediju. Pretpostavka je da je nastao indenski derivat kao glavni produkt uz nepreoreagirani početni spoj 2 te nekoliko neidentificiranih spojeva. Svi spojevi potvrđeni su 1H NMR spektroskopijom, te su na Institutu Ruđer Bošković provedeni kvantno-kemijski proračuni u cilju istraživanja reakcijskog mehanizma.

Abstract (english)

The aim of this research is to perform a quantum-chemical calculation and explain the mechanism of the thermal reaction. For this purpose, the 2-methyl-3-thiophenic derivative of o-distrylbenzene 2 was synthesized using the Wittig reaction. The Wittig reaction was carried out using the diphosphonium salt α,α'-o-xylene dibromide and 2-methyl-3-thiophene-carbaldehyde 1. The synthesis of 2-methyl-3-thiophene-carbaldehyde was carried out with the help of N,N,N-trimethylethylenediamine, n-butyllithium and mixtures of n-butyllithium and lithium diisopropylamide. The synthesized compound 2 was subjected to a thermal reaction in an acidic medium. The assumption is that the indene derivative was formed as the main product along with the unreacted initial compound 2 and several unidentified compounds. All compounds were confirmed by 1H NMR spectroscopy, and quantum chemical calculations were carried out at the Ruđer Bošković Institute in order to investigate the reaction mechanism.

• Keywords: tiofen; indanski i indenski derivati; mehanizam reakcije; termička reakcija
• Keywords (english): thiophene; indane and indene derivatives; reaction mechanism; thermal reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:969488
• Study programme: Title: Materials Science and 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: Closed access
• Created on: 2023-03-02 12:21:44