Sinteza fluoriranih sulfidov in nekatere njihove pretvorbe

magistrsko delo

Jana Krušič (Avtor), Marjan Jereb (Mentor), Mitja Kolar (Član komisije za zagovor), Krištof Kranjc (Član komisije za zagovor)

Povzetek

Kemija fluoriranih organskih molekul je sicer že precej raziskana, pa vendar zagotovo skriva še veliko presenečenj. Zaradi posebnih kemijskih in fizikalnih lastnosti (polarna vez C–F namreč sodi med najmočnejše enojne vezi) je tarča raziskovalcev že več kot sto let. Posledično je bilo do danes pripravljenih že ogromno spojin, ki se jih uporablja na raznovrstnih področjih (farmacija, industrija gospodinjskih aparatov, kemija materialov...). V prvem delu magistrskega dela sem se osredotočala na pretvorbo fluoriranih in perfluoriranih halogenidov s tiofenolom pri klasičnih pogojih nukleofilne substitucije v acetonitrilu v prisotnosti kalijevega karbonata. Sodeč po do sedaj znani literaturi, je sinteza takšnih sulfidov mogoča le po poti radikalske ali fotokemijske reakcije. V sklopu magistrskega dela smo torej skušali ugotoviti, ali drži, da sinteza res ni mogoča po poti nukleofilne substitucije. Preliminarni eksperimenti so nakazali, da bi takšen pristop lahko bil širše uporaben, saj so reakcije potekle v želeni smeri, to je do fluoriranih in perfluoriranih sulfidov. Reaktivnost nekaterih fluoriranih in perfluoriranih sulfidov sem testirala s pretvorbami v ustrezne sulfokside. Uporaba N-klorosukcinimida (NCS) kot oksidanta se je izkazala za uspešno le v primerih oksidacije fluoriranih sulfidov. V primeru perfluoriranih sulfidov reakcija z NCS ni bila uspešna. Slednje sulfide sem dalje uspešno oksidirala s 30% vodno raztopino vodikovega peroksida, kjer je najverjetneje bistvenega pomena bil reakcijski medij. V celoti sem uspešno sintetizirala devet fluoriranih sulfidov, šest perfluoriranih sulfidov in sedem ustreznih sulfoksidov.

Ključne besede

fluorirane organske molekule;fluoriranje;fluorirani sulfidi;perfluorirani sulfidi;oksidacija sulfidov;sulfoksidi;magistrska dela;

Podatki

Jezik:	Slovenski jezik
Leto izida:	2021
Tipologija:	2.09 - Magistrsko delo
Organizacija:	UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
Založnik:	[J. Krušič]
UDK:	547.279:546.16(043.2)
COBISS:	86522627
Št. ogledov:	215
Št. prenosov:	35
Ocena:	0 (0 glasov)
Metapodatki:

Ostali podatki

Sekundarni jezik:	Angleški jezik
Sekundarni naslov:	Synthesis of fluorinated sulfides and some of their further transformations
Sekundarni povzetek:	The chemistry of fluorinated organic molecules has been extensively researched, but it certainly hides many surprises. Due to special chemical and physical properties of the C–F bond (this polar bond is one of the strongest single bonds), it has been the target of researchers for more than a hundred years. As a result, a huge number of compounds have been prepared to date, which are used in various fields (pharmacy, household appliances industry, materials chemistry...). In the first part of the master's thesis, I focused on the conversion of fluorinated and perfluorinated halides with thiophenol under classical conditions of nucleophilic substitution in acetonitrile in the presence of potassium carbonate. According to the literature data known so far, the synthesis of such sulfides is possible only by a radical or photochemical reaction. As part of the master's thesis, we therefore tried to determine whether it is true that synthesis is really not possible through nucleophilic substitution. Preliminary experiments have suggested that such an approach could be more widely used, as the reactions proceeded in the desired direction, i.e. to fluorinated and perfluorinated sulfides. The reactivity of some fluorinated and perfluorinated sulfides was tested by conversion to the corresponding sulfoxides. The use of N-chlorosuccinimide (NCS) as the oxidant has been shown to be successful only in cases of oxidation of fluorinated sulfides. In the case of perfluorinated sulfides, the reaction with NCS was not successful. The latter sulfides were further successfully oxidized with a 30% aqueous solution of hydrogen peroxide, where the reaction medium was most likely essential. In total, I successfully synthesized nine fluorinated sulfides, six perfluorinated sulfides, and seven corresponding sulfoxides.
Sekundarne ključne besede:	perfluorinated sulfides;oxidation;sulfoxides;
Vrsta dela (COBISS):	Magistrsko delo/naloga
Študijski program:	1000375
Konec prepovedi (OpenAIRE):	1970-01-01
Komentar na gradivo:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo
Strani:	52 str.
ID:	13576478