Mehanokemijska sinteza trans-1,2-bis(2,3,5,6-tetrafluor-4-jodfenil)diazena i njegova kokristalizacija s o-hidroksi iminima

master's thesis

• Title (english): Mechanochemical synthesis of trans-1,2-bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene and its cocrystalization with o-hydroxy imines
• Author: Viktorija Medvarić
• Mentor: Dominik Cinčić (mentor)
• Mentor: Nikola Cindro (mentor)
• Committee member: Dominik Cinčić (predsjednik povjerenstva)
• Committee member: Nikola Cindro (član povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Nikola Bregović (član povjerenstva)
• Committee member: Vladimir Stilinović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2020-12-14, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U sklopu ovog diplomskog rada pripravljen je 1,2,4,5-tetrafluorjodanilin (itfa) koji je
korišten za izučavanje mehanokemijske sinteze trans-1,2-bis(2,3,5,6-tetrafluor-4-
jodfenil)diazena (trans-azo) i njegovog cis-izomera pri različitim reakcijskim uvjetima (trajanje
mljevenja, vrsta i količina oksidansa, količina pomoćne krutine za mljevenje te vrsta dodane
tekućine). Mogućnost nastajanja kokristala pripravljenih azo spojeva, kao donora halogenske
veze, izučavana je s odabranim akceptorima halogenske veze, iminima dobivenim
kondenzacijom o-vanilina i aromatskih amina, 3-aminoacetofenona (ov3aa) i 4-
aminoacetofenona (ov4aa). Mehanokemijska sinteza azo spojeva je praćena
visokodjelotvornom tekućinskom kromatografijom, a pripravljeni spojevi izučavani su
metodom difrakcije rentgenskog zračenja na praškastom uzorku i razlikovno-pretražnom
kalorimetrijom. Metodom difrakcije rentgenskog zračenja na jediničnom kristalu odreĎene su
molekulska i kristalna struktura kokristala (ov4aa)2(trans-azo) te dva nusprodukta sinteze
spoja itfa: 1,2,4,6,7,9-heksafluor-3,8-dijodfenazina (fzn) i njegovog kokristala (transazo)
2(fzn).

Abstract (english)

Within this diploma thesis, 1,2,4,5-tetrafluoroiodaniline (itfa) was prepared and used to study
the mechanochemical synthesis of trans-1,2-bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene
(trans-azo) and its cis-isomer under different reaction conditions (duration of grinding, type
and amount of oxidant, amount of auxiliary grinding solid and type of added liquids). The
possibility of cocrystal formation of prepared azo compounds as halogen bond donors was
studied with selected halogen bond acceptors, imines obtained by condensation of o-vanillin
and aromatic amines, 3-aminoacetophenone (ov3aa) and 4-aminoacetophenone (ov4aa). The
mechanochemical synthesis of azo compounds was monitored by high performance liquid
chromatography, and the prepared compounds were studied by X-ray powder diffraction and
differential scanning calorimetry. The molecular and crystal structures of the cocrystal
(ov4aa)2(trans-azo) and two byproducts of itfa synthesis 1,2,4,6,7,9-hexafluoro-3,8-
diiodphenazine (fzn) and its cocrystal (trans-azo)2(fzn) were determined by single-crystal Xray
diffraction.

• Keywords: azobenzen; halogenska veza; imini; kokristali; mehanokemija
• Keywords (english): azobenzene; halogen bond; imines; cocrystals; mechanochemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:217:718271
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2022-12-14
• Created on: 2021-02-16 13:04:08