diplomsko delo
Blaž Omahen (Avtor), Jernej Iskra (Mentor)

Povzetek

Fluorove organske molekule so pomembne zaradi njihove vloge v farmaciji, agrokemiji, materialih ter medicini. V okviru diplomske naloge smo študirali reakcijo fluorodehidroksiliranja z novim fluorirnim reagentom imidazolnega tipa (1,3-bis(2,6-diizopropilfenil)-2-kloro-1H-imidazol-3-ijev divodikov trifluorid), katerega prednost sta predvsem obstojnost na zraku in reaktivnost ob prisotnosti vode, poleg tega pa se lahko regenerira z vodno raztopino vodikovega fluorida. Na modelnih substratih različno substituiranih benzilnih alkoholov smo proučevali reakcijske pogoje deoksifluoriranja. Osredotočili smo se na čas, temperaturo, topilo, vrsto baze ter razmerji med substratom, reagentom in bazo. Pri glavnem modelnem substratu 4-terc-butilbenzil alkoholu smo s spreminjanjem pogojev dosegli 76-% pretvorbo v 4-terc-butilbenzil fluorid. Raziskovali smo tudi reakcijsko pot in 4-terc-butilbenzil klorid identificirali kot vmesni produkt dvostopenjskega deoksifluorirnega mehanizma. S Hammetovo enačbo smo določili konstanto reakcije ρ in iz nje sklepali o SN2 mehanizmu nukleofilne substitucije. Nekatere substituirane benzilne alkohole smo z reagentom pretvorili v pripadajoče fluoride, prav tako pa smo delovanje reagenta pokazali na nekaterih drugih tipih substratov (karboksilna kislina, alifatski alkoholi).

Ključne besede

nukleofilno fluoriranje;deoksifluoriranje;reagent imidazolnega tipa;benzilni alkoholi;Hammetova korelacija;diplomska dela;

Podatki

Jezik: Slovenski jezik
Leto izida:
Tipologija: 2.11 - Diplomsko delo
Organizacija: UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
Založnik: [B. Omahen]
UDK: 547.1:546.16(043.2)
COBISS: 165247491 Povezava se bo odprla v novem oknu
Št. ogledov: 204
Št. prenosov: 25
Ocena: 0 (0 glasov)
Metapodatki: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Ostali podatki

Sekundarni jezik: Angleški jezik
Sekundarni naslov: Study of nucleophilic fluorination of alcohols with imidazole type of reagent
Sekundarni povzetek: Fluorinated organic molecules are important for their role in pharmaceuticals, agrochemicals, materials and medicine. In this thesis we have studied reaction of fluorodehydroxylation with the imidazole-type reagent (2-chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium dihydrogen trifluoride), which has the advantage of being stable under ambient conditions and reactive in the presence of water, while it can be regenerated using aqueous solution of hydrogen fluoride. The deoxyfluorination was studied on model substrates of differently substituted benzyl alcohols. The focus was on time, temperature, solvent, type of base, and the ratio of substrate, reagent and base. For the main model substrate 4-tert-butylbenzyl alcohol, 76% conversion to 4-tert-butylbenzyl fluoride was achieved by varying the conditions. The reaction pathway was also investigated and 4-tert-butylbenzyl chloride was identified as an intermediate product of the two-step deoxyfluorination mechanism. The Hammett equation was used to determine the reaction constant ρ and the SN2 mechanism of the nucleophilic substitution was derived. Some other substituted benzylic alcohols were converted to the corresponding fluorides with the reagent, and the activity of the reagent was also demonstrated on some other types of substrates (carboxylic acid, aliphatic alcohols).
Sekundarne ključne besede: nucleophilic fluorination;deoxyfluorination;imidazole-type reagent;benzylic alcohols;Hammet correlation;Fluor;Imidazoli;Kemijske reakcije;Univerzitetna in visokošolska dela;
Vrsta dela (COBISS): Diplomsko delo/naloga
Študijski program: 1000373
Konec prepovedi (OpenAIRE): 1970-01-01
Komentar na gradivo: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Strani: 48 str.
ID: 19876360