Primjena 1,3,5-trihidroksi-2,4,6-trinitrobenzena kao građevnog bloka u kristalnom inženjerstvu

master's thesis

• Title (english): Use of 1,3,5-trihydroxy-2,4,6-trinitrobenzene as a building block in crystal engineering
• Author: Kristina Smokrović
• Mentor: Vladimir Stilinović (mentor)
• Committee member: Vladimir Stilinović (predsjednik povjerenstva)
• Committee member: Rosana Ribić (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: 2016-06-15, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U sklopu diplomskog rada pripravljeno je te strukturno i termicki okarakterizirano devetnaest
soli i dva kokristala 1,3,5-trihidroksi-2,4,6-trinitrobenzen (trinitrofloroglucinol)
s alifatskim i aromatskim aminima te heterociklickim spojevima. Trinitrofloroglucinola
pripravljen je nitriranjem 1,3,5-trihidroksibenzena. Soli i kokristali trinitrofloroglucinola
pripravljeni su sporom evaporacijom otapala iz otopina koje sadrže trinitrofloroglucinol
i organski spoj u odgovarajucem stehiometrijskom omjeru. Produkti su
analizirani difrakcijom rentgenskog zracenja na jedinicnom kristalu, razlikovnom pretražnom
kalorimetrijom i spektroskopijom u infracrvenom podrucju.
NaÒeno je da trinitrofloroglucinol može sudjelovati u velikom broju meÒumolekulskih
vodikovih veza jer sadrži veliki broja akceptora vodikove veze s obzirom na broj
atoma u molekuli. Unutarmolekulske vodikove veze izmeÒu protoniranih hidroksilnih
skupina i susjednih nitro-skupina stabilizirane potpomognute su rezonancijom i
delokalizacijom naboja te su slabi donori vodikove veze. To cini trinitrofloroglucinol
odlicnim modelnim spojem za proucavanje utjecaja strukture molekule donora vodikove
veze na strukturu kristala.

Abstract (english)

Nineteen salts and two co-crystals of 1,3,5-trihydroxy-2,4,6-trinitrobenzene (trinitrophloroglucinol)
with heterocyclic compounds, aliphatic, and aromatic amines, were prepared
and structurally and thermically characterised. Trinitrophloroglucinol was prepared
from 1,3,5-trihydroxybenzene by nitration. Salts and cocrystals were prepared
by slow evaporation of solvent from a solution containing trinitrophloroglucinol and
an organic compound in an appropriate stoichiometric amount. Resulting compounds
were analyzed by diffraction of X-rays on single crystals, differential scanning calorimetry
and infra-red spectroscopy.
Trinitrophloroglucinol can participate in a great number of intermolecular hydrogen
bonds because it contains a large number of hydrogen bond donors compared to
the total number of atoms in the molecule. The protonated hydroxyl groups and adjacent
nitro-groups are bonded by charge- and resonance-assisted hydrogen bonds and
therefore are weak hydrogen bond donors. This makes trinitrophloroglucinol an ideal
model compound for studying the effects of hydrogen bond donor molecule structure
on crystal structure.

• Keywords: kristalni inženjering; rentgenska strukturna analiza; trinitrofloroglucinol; vodikove veze
• Keywords (english): crystal engineering; hydrogen bonds; trinitrophloroglucinol; X-ray structural analysis
• Language: croatian
• URN:NBN: urn:nbn:hr:217:455700
• 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: 2018-06-15
• Created on: 2017-03-22 13:47:39