Jodoform - zaboravljeni donor halogenske veze

master's thesis

• Title (english): Iodoform -a forgotten halogen bond donor
• Author: Tino Šeba
• Mentor: Vladimir Stilinović (mentor)
• Committee member: Vladimir Stilinović (predsjednik povjerenstva)
• Committee member: Nives Galić (član povjerenstva)
• Committee member: Josip Požar (član povjerenstva)
• Committee member: Dominik Cinčić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2018-09-28, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U sklopu ovog diplomskog rada izučavan je potencijal jodoforma kao donora halogenske veze
pripremom kokristala jodoforma s nizom neutralnih i ionskih akceptora halogenske veze. S
neutralnim ditopičnim akceptorima halogenske veze kao što su 4,4'-bipiridin, 1,4-
diazabiciklo[2.2.2]oktan jodoform tvori kokristale. Pokušaj pripreme ekvivalentne strukture s
N,N,N’,N’-tetrametiletilendiaminom kao akceptorom halogenske veze jodoform kokristalizira
s jodidom monoprotoniranog N,N,N’,N’-tetrametiletilendiamina zbog raspada jodoforma u
prisutstvu tetrametiletilendiamina. To nas je otkriće navelo da istražimo kokristalizaciju
jodoforma i organskih jodida detaljnije. Jodoform tvori kokristale sa sljedećim N-metil-3-
supstituiranim piridinijevim jodidima: N-metil-3-metilpiridinijevim jodidom, N-metil-3-
klorpiridinijevim jodidom, N-metil-3-brompiridinijevim jodidom, N-metil-3-jodpiridinijevim
jodidom i N-metil-3-(metoksikarbonil) piridinijevim jodidom. Uspješno su još priređeni
kokristali jodoforma s N-metil-2,4,6-trimetilpiridinijevim jodidom te s dva kvarterna
ditopična amonijeva dijodida: N,N,N,N’,N’,N’-heksametiletilendiamonijeva dijodida i 1,4-
dimetil-1,4-diazabiciklo[2.2.2]oktan-1,4-diijeva dijodida. U svim tim kokristalima jodidni ion
akceptor je halogenske veze i većinom vodikove veze C–H∙∙∙I− što dovodi do stvaranja
anionskih mreža čije geometrije i topologije ovise o steričkim svojstvima organskih kationa.

Abstract (english)

Within this master thesis the potential of iodoform as a halogen bond donor was studied by
preparing cocrystals of iodoform with a series of neutral and ionic halogen bond acceptors.
With neutral ditopic electron donors such as 4,4'-bipyridine and 1,4-diazabicyclo[2.2.2]octane
iodoform was found to form cocrystals. An attempt to prepare an equivalent structure with
N,N,N’,N’-tetramethylethylenediamine yielded cocrystal of iodoform with iodide salt of
monoprotonated tetramethylethylenediamine. This has prompted us to study the
cocrystallisation of iodoform with iodides of organic cations in more detail. Iodoform was
found to form cocrystals with following N-methyl-3-methylpiridinium iodides: N-methyl-3-
methylpiridinium iodide, N-methyl-3-chloropiridinium iodide, N-methyl-3-bromopiridinium
iodide, N-methyl-3-iodopiridinium iodide and N-methyl-3-(methoxycarbonyl)piridinium
iodide. Also, iodoform forms cocrystals with N-methyl-2,4,6-trimethylpiridinium iodide,
N,N,N,N',N',N'-hexamethylethylenediamonium diodide and 1,4-dimethyl-1,4
diazabicyclo[2.2.2]octane-1,4-diium diiodide. In all those cocrystals, the iodide anion acts as
halogen bond and frequently hydrogen bond acceptor forming anionic networks, the
geometries and topologies of which are determined by the steric properties of the counterion.

• Keywords: halogenska veza; jodoform; kristalno inžinjerstvo; kokristali
• Keywords (english): halogen bond; iodoform; crystal engineering; cocrystals
• Language: croatian
• URN:NBN: urn:nbn:hr:217:343712
• 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: 2020-09-28
• Created on: 2018-11-23 12:59:20