Sinteza i spektroskopska karakteristika novih derivata fenantrena i nafto[2,1-b]tiofena

undergraduate thesis

• Title (english): Synthesis and spectroscopic characterization of novel phenantrene and naphtho[2,1-b]thiophene derivatives
• Author: Matej Kadić
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Nataša Perin (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2017-09-05, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

Cilj ovog rada bio je sintetizirati nove amido supstituirane derivate nafto[2,1-b]tiofena 7-8 i amido supstituirane derivate fenantrena 14-15. Za pripravu ciljnih spojeva korištene su klasične metode organske i fotokemijske sinteze. Aciklički derivati akrilonitrila 3 i 10 priređeni su kondenzacijom aldehida i odgovarajućih acetonitrila. Bazičnom hidrolizom cikličkih cijano derivata 4 i 11 priređene su odgovarajuće karboksilne kiseline 5 i 12. Amido supstituirani derivati nafto[2,1-b]tiofena 7-8 priređeni su iz nafto[2,1-b]tiofen-9-karbonil-klorida 6 reakcijom s odgovarajućim aminima, dok je amido supstituirani derivat fenantrena 15 priređen iz fenantren-9-karbonil-klorida 13. Strukture svih novo priređenih spojeva potvrđene su 1H NMR i 13C NMR spektroskopijom. Sinteza amido supstituiranog derivata fenantrena 14 nije bila uspješna.

Abstract (english)

The intention of this study was to synthesize new amido substituted derivatives of naphto[2,1-b]thiophenes 7-8 and amido supstituted derivatives of phenanthrenes 14-15. For the synthesis of target compounds classical methods of organic synthesis and photochemical synthesis were used. Acyclic acrylonitriles 3 and 10 were obtained in the condensation of aldehydes and corresponding acetonitriles. Carboxylic acids 5 and 12 were prepared by basic hydrolysis of cyano substituted derivatives 4 and 11. Amido supstituted derivatives of naphto[2,1-b]thiophene 7-8 were prepared from naphto[2,1-b]thiophene-9-carbonyl-chloride 6 in the nucleophilyc substitution reaction with the appropriate amines, and amido substituted derivative of phenanthrene 15 was prepared from phenanthrene-9-carbonyl-chloride 13. Synthesis of amido derivativeof phenanthrene 14 was not successful. The structures of all newly synthesizes compounds were confirmed by means of 1H NMR and 13C NMR spectroscopy.

• Keywords: amidi; fenantren; nafto[2 1-b]tiofen; organska sinteza; 1H NMR i 13C NMR spektroskopija
• Keywords (english): amides; phenanthrene; naphto[2 1-b]thiophene; organic synthesis; 1H NMR and 13C NMR spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:342173
• Study programme: Title: Chemical 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: Open access
• Created on: 2021-01-08 12:51:52