Priprava i studij vezivanja permetiliranih diamantoidnih amonijevih soli s ciklodekstrinima

master's thesis

• Title (english): Synthesis and binding study of permathylated diamondoid ammonium salts with cyclodextrines
• Author: Ruža Jozepović
• Mentor: Marija Alešković (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Nikola Bregović (član povjerenstva)
• Committee member: Nikola Cindro (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2020-09-30, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U okviru ovog rada provedena je sinteza N,N,N-trimetiladamantan-1-amonijevog jodida (1),
N,N,N-trimetildiamantan-4-amonijevog jodida (2) i N,N,N,N',N',N'-heksametildiamantan-4,9-
diamonijevog dijodida (3). Amonijeva sol 1 pripravljena je permetiliranjem komercijalno
dostupnog 1-aminoadamantana dok su spojevi 2 i 3 sintetizirani slijedom reakcija počevši od
diamantanskog ugljikovodika. Svi pripravljeni spojevi okarakterizirani su uobičajenim analitičkim
tehnikama, a ciljne molekule 1–3 zatim su ispitivane kao molekule gosti kod kompleksiranja s β- i
γ-ciklodekstrinima u vodenim otopinama.
Studij vezivanja molekula 1–3 s β- i γ-ciklodekstrinima proveden je titracijskim 1H NMR
eksperimentima u D2O otopinama te se temeljem dobivenih rezultata zaključuje da nastaju
kompleksi između β-ciklodekstrina i gosta 1 odnosno 2 te γ-ciklodekstrina i gosta 2. Svi navedeni
kompleksi su 1:1 stehiometrije uz vrijednosti konstanti stabilnosti ≥ 103 mol–1 dm3.

Abstract (english)

In the scope of this work synthesis of N,N,N-trimethyladamantane-1-ammonium iodide (1),
N,N,N-trimethyldiamantane-4-ammonium iodide (2) and N,N,N,N',N',N'-hexamethyldiamantane-
4,9-diammonium diiodide (3) was performed. Ammonium salt 1 was prepared by permethylation
of commercially available 1-aminoadamantane while compounds 2 and 3 were prepared through a
series of reactions starting from the diamantane hydrocarbon. All synthesized compounds were
characterized by usual analytical techniques and target molecules 1–3 were then tested as guest
molecules in complexation with β- and γ-cyclodextrins in aqueous solutions.
Binding studies of molecules 1–3 with β- and γ-cyclodextrins were performed using 1H NMR
titration experiments in D2O solutions and the obtained results demonstrated that complexes of β-
cyclodextrin and guests 1 or 2, respectively and γ-cyclodextrin and guest 2 were formed. All the
observed complexes were of a 1:1 stoichiometry with the values of stability constants ≥ 103 mol–1
dm3.

• Keywords: ciklodekstrini; diamantoidi; inkluzijski kompleksi; konstante stabilnosti; NMR titracija
• Keywords (english): cyclodextrins; diamondoids; inclusion complexes; NMR titration; stability constants
• Language: croatian
• URN:NBN: urn:nbn:hr:217:198573
• 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: 2022-10-01
• Created on: 2020-10-16 09:56:46