20.500.12556/DKUM-85578 Razvoj sintezne metode za pripravo biarilov z Ullmannovo reakcijo diplomsko delo univerzitetnega študijskega programa I. stopnje Development of a synthesis method for the preparation of biaryls using the Ullmann reaction V diplomskem delu je predstavljena sinteza in karakterizacija biarila N-benzilanilina, ki smo ga sintetizirali z Ullmannovo reakcijo po mehanizmu križnega spajanja (angl. cross coupling). Z namenom pridobitve čistega produkta s čim višjimi izkoristki smo reakcije sinteze izvedli z optimiziranjem treh reakcijskih pogojev, in sicer temperature, časa reakcije in atmosfere, v kateri je reakcija potekala. Končne produkte Ullmannove reakcije smo okarakterizirali z infrardečo in jedrsko magnetno spektroskopijo. Z infrardečo spektroskopijo smo potrdili nastanek biarila N-benzilanilina pri vseh testnih reakcijah, v nekaterih primerih tudi prisotnost benzilamina oz. jodobenzena. Z jedrsko magnetno resonanco smo potrdili njihovo kemijsko strukturo in določili njihovo razmerje v vzorcu. Ugotovili smo, da višje izkoristke N-benzilanilina dosegamo z reakcijami, ki jih izvedemo v dušikovi atmosferi pri 80°C in trajajo dlje časa, pri reakcijah na zraku pa N-benzilanilin oksidira do N- benzilidenanilina, ki se pojavlja v produktu v višjih koncentracijah. This work presents the synthesis and characterization of biaryl N-benzylaniline synthesized by the Ullmann reaction using the cross-coupling mechanism. In order to obtain a pure product with the highest possible yield, the synthesis reactions were carried out by optimizing three reaction conditions, namely temperature, reaction time and the atmosphere in which the reaction took place. The final products of the Ullmann reaction were characterized by infrared and nuclear magnetic spectroscopy. Infrared spectroscopy confirmed the formation of biaryl N-benzylaniline in all test reactions, and in some cases the presence of benzylamine or iodobenzene. Using nuclear magnetic resonance, we confirmed their chemical structure and determined their ratio in the sample. We found that higher yields of N-benzylaniline are obtained with reactions carried out in a nitrogen atmosphere at 80°C and lasting longer, while reactions in air oxidize N-benzylaniline to N-benzylideneaniline, which appears in the product in higher concentration. Ullmannova reakcija križno spajanje biarili N-benzilanilin FTIR NMR Ullmann reaction cross coupling biaryls N-benzylaniline FTIR NMR true true false [Ž. Škrinjarič] Slovenski jezik Angleški jezik Diplomsko delo/naloga 2023-09-01 20:46:03 2023-09-11 13:15:52 2023-10-06 03:23:50 0000-00-00 00:00:00 2023 0 Maribor 0 Maribor 1 spletni vir (1 datoteka PDF (VIII, 33 f.)) 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 66.095.257(043.2) 167172867 UN_Skrinjaric_Ziga_2023.pdf UN_Skrinjaric_Ziga_2023.pdf 1 E9B23B960C625768DCA2EDA6533C083C 88f7b365c6cd82f00b58b70871f487b7bb90b0a1d47f2fa2483bca0438a2a990 b6fab56f-5090-11ee-a242-00155d000105 https://dk.um.si/Dokument.php?lang=slv&id=171956 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0