20.500.12556/RUL-183205 Sinteza in reaktivnost mezoionskih N-heterocikličnih olefinov s triazolnim ogrodjem Synthesis and reactivity of triazole based mesoionic N-heterocyclic olefins V doktorskem delu smo raziskovali mezoionske N-heterociklične olefine (mNHO). mNHO so nova skupina ligandov, ki izhajajo iz strukturno podobnih (mezoionskih) N-heterocikličnih karbenov, ki so zelo razširjeni ligandi. Opisali smo njihovo sintezo iz 1,3,4,5-substituiranih-1,2,3-triazolijevih soli, nato pa smo preizkusili njihovo reaktivnost z različnimi organokovinskimi prekurzorji. Zanimale so nas koordinativne lastnosti mNHO, zato smo sintetizirali mNHO, ki bi lahko omogočili monodentatno in bidentatno koordinacijo na kovinski center ter uvedbo stereogenega centra v organokovinski kompleks. Pripravili smo prve znane paladijeve in zlatove komplekse z mNHO. Njihove strukture smo potrdili s spektroskopskimi in računskimi metodami. Opisali smo tudi redek primer konformacijsko stabilne stereogene osi C(sp$^2$)–C(sp$^3$) v enem od paladijevih kompleksov. Poleg tega smo pripravili še stabilen Lewisov adukt mNHO z BH$_3$. Njegovo reaktivnost smo preizkusili v reakcijah redukcije aldehidov in ketonov. Ugotovili smo, da ima mNHO-BH$_3$ večjo aktivnost od sorodnih NHC-boranov in MIC-boranov, saj za redukcijo aldehidov niso bili potrebni nobeni aditivi. In this doctoral thesis, we investigated mesoionic N-heterocyclic olefins (mNHOs). mNHOs are a recent class of ligands, derived from structurally similar (mesoionic) N-heterocyclic carbenes, which are widely used as ligands. We described preparation of mNHOs from 1,3,4,5-substituted-1,2,3-triazolium salts and tested their reactivity towards different organometallic precursors. Our focus was on mNHOs’ coordination abilities and properties of their organometallic compounds. We therefore synthesised mNHOs that could enable monodentate and bidentate coordination to the metal center and introduce a stereogenic centre into the organometallic complex. We successfully prepared the first known palladium and gold complexes with mNHOs. Their structures were confirmed using spectroscopic and computational methods. We also described a rare instance of a conformationally stable C(sp$^2$)–C(sp$^3$) stereogenic axis in one of the palladium complexes. Additionally, we prepared a stable Lewis adduct of mNHO with BH$_3$. We tested its reactivity for aldehyde and ketone reductions. Our findings indicate that, compared to related NHC-boranes and MIC-boranes, mNHO-BH$_3$ exhibits higher activity, as no additives were required for the successful reduction of aldehydes. 1 2 3-triazoli mezoionski N-heterociklični olefini koordinacija paladijev kompleks 1 2 3-triazoles mesoionic N-heterocyclic olefins coordination palladium complex true false false Slovenski jezik Angleški jezik Doktorsko delo/naloga 2026-06-08 10:10:02 2026-06-08 10:10:03 2026-08-26 12:06:24 0000-00-00 00:00:00 2026 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 20621 286866435 Zevart_Tisa_-_Sinteza_in_reaktivnost_mezoionskih_N-heterociklicnih_olefinov_s_triazolnim_ogrodje.pdf Zevart_Tisa_-_Sinteza_in_reaktivnost_mezoionskih_N-heterociklicnih_olefinov_s_triazolnim_ogrodje.pdf 1 C9F3FFBC43C53AA4212CCA8C49A8EB9B eeb17182e10aed4c10ff147ae50aa0828e7a1b554740d80bb16a6810cdbd0524 729b72d9-6311-11f1-9b0d-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=235082 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0