Kristalno inženjerstvo kokristala iminâ s novim motivima halogenske veze

master's thesis

• Title (english): Crystal engineering of imines cocrystals with novel halogen bond motifs
• Author: Matea Vitković
• Mentor: Dominik Cinčić (mentor)
• Committee member: Dominik Cinčić (predsjednik povjerenstva)
• Committee member: Sanda Rončević (član povjerenstva)
• Committee member: Josip Požar (član povjerenstva)
• Committee member: Vladimir Stilinović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2016-11-24, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Inorganic Chemistry

Abstract

U sklopu ovog diplomskog rada pripravljeni su imini kondenzacijom o-vanilina (ov) i amina: 3- i 4-aminoacetofenona (3aa i 4aa) te 2-aminonaftalena (2an). Mehanokemijskom sintezom i kristalizacijom iz otopine izučavana je mogućnost nastajanja kokristala iminâ sa sljedećim donorima halogenske veze: 1,2- i 1,4-dijodtetrafluorbenzenom (1,2-tfib i 1,4-tfib), 1,4-dibromtetrafluorbenzenom (1,4-tfbb), jodpentafluorbenzenom (ipb), N-bromsukcinimidom (NBS) te N-bromftalimidom (NBF). Pripravljeni spojevi izučavani su metodom difrakcije rentgenskih zraka na praškastom uzorku i razlikovno-pretražnom kalorimetrijom. Metodom difrakcije rentgenskog zračenja na jediničnom kristalu iznađene su molekulske i kristalne strukture triju kokristala s perfluoriranim donorima halogenske veze te dviju polimofnih formi produkta nastalog bromiranjem i ciklizacijom ov2an-a. U svim su kokristalima molekule donora ditopične i povezuju se s molekulama iminâ halogenskim vezama IO. U kokristalu (ov3aa)2(1,4-tfib) su akceptori halogenske veze karbonilne skupine imina, a u (ov2an)2(1,4-tfib) hidroksilne i metoksi skupine koje stvaraju strukturni motiv s bifurkiranim donorom halogenske veze. U (ov4aa)(1,2-tfib) prisutna su oba strukturna motiva halogenske veze, u kojima je 1,2-tfib povezan bifurkirano s hidroksilnom i metoksi skupinom jedne molekule imina, te monofurkirano s karbonilnom skupinom druge molekule.

Abstract (english)

Within this master thesis the imines were prepared through condensation of o-vanillin (ov) and amines (3- and 4-aminoacetophenone and 2-aminonaphtalene, 3aa, 4aa and 2an, respectively). The possibility of cocrystallization of the imines and six halogen bond donors: 1,2- and 1,4-diiodotetrafluorobenzene (1,2-tfib and 1,4-tfib), 1,4-dibromotetrafluorobenzene (1,4-tfbb), iodopentafluorobenzene (ipb), N-bromosuccinimide (NBS) and N-bromophtalimide (NBF), was investigated by means of mechanochemical synthesis and crystalization from solution. The crystals were described by powder X-ray diffraction and differential scanning calorimetry. The crystal and molecular structures of three prepared cocrystals with perfluorinated halogen bond donors and two polymorphs of an imine bromination and cyclization product were explored by single crystal X-ray diffraction. In all cocrystals, the donor molecules are ditopic and connected to the imine molecules via IO halogen bonds. In the cocrystal (ov3aa)2(1,4-tfib) the acceptors of halogen bonds are the carbonyl groups of ov3aa molecules and in (ov2an)2(1,4-tfib) the 1,4-tfib molecules are bifurcatedly connected to hydroxy and methoxy groups of the ov2an molecule. In (ov4aa)(1,2-tfib) the 1,2-tfib molecules are connected bifurcatedly to hydroxy and methoxy groups of one ov4aa molecule and monofurcatedly to the carbonyl group of the other imine molecule. synthesis.

• Keywords: halogenska veza; imini; kokristali; mehanokemijska sinteza
• Keywords (english): halogen bond; imine; cocrystals; mechanochemical synthesis
• Language: croatian
• URN:NBN: urn:nbn:hr:217:303704
• 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
• Created on: 2017-01-27 12:01:02