Kokristalizacija perhalogeniranih donora halogenske veze s iminima izvedenima iz 2-nitrobenzaldehida i aromatskih amina

master's thesis

• Title (english): Cocrystalization of perhalogenated halogen bond donors with imines derived from 2-nitrobenzaldehyde and aromatic amines
• Author: Leon Poljanić
• Mentor: Dominik Cinčić (mentor)
• Committee member: Dominik Cinčić (predsjednik povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Tajana Begović (član povjerenstva)
• Committee member: Vladimir Stilinović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2023-02-14, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U sklopu ovog diplomskog rada pripravljeni su imini izvedeni iz 2-nitrobenzaldehida i
aromatskih amina (4-, 3- i 2-halogenanilini, halogen = Cl, Br, I; te 3-nitroanilin).
Mehanokemijskom sintezom i kristalizacijom iz otopine izučavana je mogućnost nastajanja
kokristala pripravljenih imina s odabranim perhalogeniranim donorima halogenske veze s
ciljem da se istraži potencijal različitih funkcijskih skupina imina koje se mogu ponašati kao
akceptori halogenske veze. Dobiveni produkti okarakterizirani su difrakcijom rentgenskog
zračenja na polikristalnom uzorku, metodama termičke analize i računalnim metodama. Za
devet kokristala metodom difrakcije rentgenskog zračenja na jediničnom kristalu određene su
molekulske i kristalne strukture. Strukturnom analizom utvrđeno je da je u većini kokristala
dominantna supramolekulska interakcija halogenska veza N⸱⸱⸱I koja se ostvaruje između atoma
joda perhalogeniranog donora halogenske veze i atoma dušika iminske skupine. U pet
kokristala molekule imina se dodatno povezuju pnikogenskom vezom N⸱⸱⸱O koja se ostvaruje
između atoma dušika i atoma kisika nitro skupina susjednih imina.

Abstract (english)

As a part of this thesis, imines were prepared from 2-nitrobenzaldehyde and aromatic amines
(4-, 3- i 2-halogenanilines, halogen = Cl, Br, I; and 3-nitroaniline). The investigation of
cocrystal synthesis from prepared imines and selected halogen bond donors was carried out
using mechanochemical synthesis and crystallization from solution, in order to research the
possibilities of different functional groups to act as halogen bond acceptors. The obtained
products were characterized by X-ray diffraction methods, by thermal analysis methods and
computational methods. For nine cocrystals, crystal and molecular structures were determined
using single-crystal X-ray diffraction. Structural analysis has shown N⸱⸱⸱I halogen bond
between the perhalogenated halogen bond donor's iodine atom and imine nitrogen atom as the
dominant supramolecular interaction in most cocrystals. In five cocrystals imine molecules are
additionally connected via pnicogen bond N⸱⸱⸱O between nitro group nitrogen and oxygen
atoms of neighbouring imines.

• Keywords: kokristali; kristalno inženjerstvo; halogenska veza; pnikogenska veza
• Keywords (english): cocrystals; crystal engineering; halogen bond; pnicogen bond
• Language: croatian
• URN:NBN: urn:nbn:hr:217:932328
• Project: Number: IP-2019-04-1868; Title: Nove građevne jedinke u supramolekulskom dizajnu složenih višekomponentnih molekulskih kristala temeljenih na halogenskim vezama; Title: New building blocks for the supramolecular design of complex multi-component molecular crystals based on halogen bonds; Acronym: HaloBond; Leader: Dominik Cinčić; 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: 2024-02-14
• Created on: 2023-02-16 15:18:29