Konformacijska i vibracijska analiza N-supstituiranih imidazolijevih 2-aldoksima

master's thesis

• Title (english): Conformational and vibrational analysis of N-substituted imidazole 2-aldoximes
• Author: Tomislav Ilievski
• Mentor: Tomica Hrenar (mentor)
• Committee member: Tomica Hrenar (predsjednik povjerenstva)
• Committee member: Višnja Vrdoljak (član povjerenstva)
• Committee member: Snežana Miljanić (član povjerenstva)
• Committee member: Gordan Horvat (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2021-09-30, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Aldoksimi su skupina organskih spojeva strukturne formule RCH=NOH (oksimi aldehida) čiju
primjenu nalazimo u medicini kao reaktivatore enzima acetil- i butirilkolinesteraze nakon
izloženosti organofosfornim spojevima te kao potencijalne agense s antimikrobnim
djelovanjem. U sklopu ovog rada istraživana su prethodno sintetizirana dva nova aldoksima,
(E)-N-benzilimidazol-2-karbaldoksim i (E)-N-benzil-2-hidroksiiminometil-3-metilimidazolijev bromid, korištenjem transmisijske infracrvene spektroskopije i Ramanove spektroskopije.
Za oba spoja provedena su teorijska istraživanja koja su uključivala potpunu konformacijsku
analizu spojeva metodom holističkog pretraživanja na višedimenzijskoj koordinatnoj
hiperrešetki te kvantno-kemijske izračune harmoničkih i anharmoničkih infracrvenih i
Ramanovih spektara. Proračuni su provedeni za najzastupljenije konformere korištenjem teorije
funkcionala gustoće na B3LYP-D3/6-311++G(d,p) razini teorije. Na temelju tih rezultata
određeni su potpuni konformacijski prostori, a usporedbom i analizom teorijskih te
eksperimentalnih vibracijskih spektara asignirane su najvažnije vibracijske vrpce u
vibracijskim spektrima.

Abstract (english)

Aldoximes are a group of organic compounds with structural formula RCH=NOH (oximes of
aldehydes) which are used in medicine as reactivators of the acetyl- and butyrylcholinesterase
enzymes after exposure to organophosphorus compounds and as potential antimicrobial agents.
In this thesis two previously synthesized aldoximes, (E)-N-benzylimidazole-2-carbaldoxime
and (E)-N-benzyl-2-hydroxyiminomethyl-3-methylimidazolium bromide, were investigated
using Infrared transmission spectroscopy and Raman spectroscopy. For both coumpounds a
computational study involving conformational analysis using grid search method on
multidimensional hyper grid and quantum-chemical calculations of anharmonic and hamornic
Infrared and Raman spectra were performed. Calculations were performed for conformers with
most significant content using density functional theory at the B3LYP-D3/6-311++G(d,p) level
of theory. Based on these results complete conformational spaces were determined, and by
comparison and analysis of theoretical and experimental vibrational spectra, most important
vibrational bands in vibrational spectra were assigned.

• Keywords: DFT; IR; konformacijska analiza; Raman; vibracijska analiza
• Keywords (english): conformational analysis; DFT; IR; Raman; vibrational analysis
• Language: croatian
• URN:NBN: urn:nbn:hr:217:753469
• Project: Number: IP-2016-06-3775; Title: Aktivnošću i in silico usmjeren dizajn malih bioaktivnih molekula; Title: Activity and in silico guided design of bioactive small molecules; Acronym: ADESIRE; Leader: Tomica Hrenar; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• 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: 2023-09-30
• Created on: 2021-10-25 12:27:20