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master's thesis
PRIPRAVA LIPOFILNIH TRIAZOLNIH DERIVATA PROPARGILAMINA KLIK-REAKCIJAMA KEMIJA ALKINA U NOVOM NASTAVNOM PROGRAMU KEMIJE
Zagreb: University of Zagreb, Faculty of Science, 2020. urn:nbn:hr:217:036634
Hamer, Dominik
University of Zagreb
Faculty of Science
Department of Biology
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Hamer, D. (2020). PRIPRAVA LIPOFILNIH TRIAZOLNIH DERIVATA PROPARGILAMINA KLIK-REAKCIJAMA KEMIJA ALKINA U NOVOM NASTAVNOM PROGRAMU KEMIJE (Master's thesis). Zagreb: University of Zagreb, Faculty of Science; Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:036634

Hamer, Dominik. "PRIPRAVA LIPOFILNIH TRIAZOLNIH DERIVATA PROPARGILAMINA KLIK-REAKCIJAMA KEMIJA ALKINA U NOVOM NASTAVNOM PROGRAMU KEMIJE." Master's thesis, University of Zagreb, Faculty of Science; University of Zagreb, Faculty of Science, 2020. https://urn.nsk.hr/urn:nbn:hr:217:036634

Hamer, Dominik. "PRIPRAVA LIPOFILNIH TRIAZOLNIH DERIVATA PROPARGILAMINA KLIK-REAKCIJAMA KEMIJA ALKINA U NOVOM NASTAVNOM PROGRAMU KEMIJE." Master's thesis, University of Zagreb, Faculty of Science; University of Zagreb, Faculty of Science, 2020. https://urn.nsk.hr/urn:nbn:hr:217:036634

Hamer, D. (2020). 'PRIPRAVA LIPOFILNIH TRIAZOLNIH DERIVATA PROPARGILAMINA KLIK-REAKCIJAMA KEMIJA ALKINA U NOVOM NASTAVNOM PROGRAMU KEMIJE', Master's thesis, University of Zagreb, Faculty of Science; University of Zagreb, Faculty of Science, accessed 19 May 2024, https://urn.nsk.hr/urn:nbn:hr:217:036634

Hamer D. PRIPRAVA LIPOFILNIH TRIAZOLNIH DERIVATA PROPARGILAMINA KLIK-REAKCIJAMA KEMIJA ALKINA U NOVOM NASTAVNOM PROGRAMU KEMIJE [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; Zagreb: University of Zagreb, Faculty of Science; 2020 [cited 2024 May 19] Available at: https://urn.nsk.hr/urn:nbn:hr:217:036634

D. Hamer, "PRIPRAVA LIPOFILNIH TRIAZOLNIH DERIVATA PROPARGILAMINA KLIK-REAKCIJAMA KEMIJA ALKINA U NOVOM NASTAVNOM PROGRAMU KEMIJE", Master's thesis, University of Zagreb, Faculty of Science, Zagreb; University of Zagreb, Faculty of Science, Zagreb, 2020. Available at: https://urn.nsk.hr/urn:nbn:hr:217:036634

Metadata
TitlePRIPRAVA LIPOFILNIH TRIAZOLNIH DERIVATA PROPARGILAMINA KLIK-REAKCIJAMA KEMIJA ALKINA U NOVOM NASTAVNOM PROGRAMU KEMIJE
Title (english)Preparation of lipophilic triazole derivatives of propargylamine by click reactions Alkyne chemistry in new chemistry syllabus
AuthorDominik Hamer
MentorVesna Petrović Peroković (mentor)
MentorNenad Judaš (mentor)
Committee memberVesna Petrović Peroković (predsjednik povjerenstva)
Committee memberNenad Judaš (član povjerenstva)
Committee memberMirela Sertić Perić (član povjerenstva)
Committee memberIvana Maguire (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Biology)
Zagreb
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2020-09-30, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U okviru istraživačkog dijela diplomskog rada opisana je priprava lipofilnih alifatskih azida (dodecil, heksadecil) te kolesterol-azida potrebnih za sintezu 1,4-disupstituiranih triazolnih derivata. Alifatski azidi pripravljeni su reakcijom supstitucije iz odgovarajućih alkil-bromida i natrijevog azida, dok je kolesterolazid pripravljen iz kolesterol-mesilata. Sva tri azida te prethodno pripravljeni 2-(adamantan-1-il)etil-azid u reakciji s propargilaminom prevedeni su u nove 1,4-disupstituirane 1,2,3-triazole bakrom(I) kataliziranom azid-alkinskom 1,3-dipolarnom cikloadicijom (CuAAC). Klik-reakcija provedena je u prisutnosti di-tertbutil- dikarbonata (Boc2O) pri čemu je istodobno zaštićena amino-skupina propargilamina. Uklanjanjem Boc zaštite u prisutnosti trifluoroctene kiseline pripravljeni su triazolni derivati propargilamina, ciljne molekule ovog rada. Struktura svih pripravljenih spojeva potvrđena je uobičajenim analitičkim metodama – spektroskopijom NMR (1H i 13C), infracrvenom spektroskopijom (IR) i spektrometrijom masa (MS). U metodičkom dijelu rada prikazana je usporedba nastavnih sadržaja i udžbenika pisanih prema novom i starom kurikulumu vezanih uz kemiju alkina u osnovnoj i srednjoj školi. Osmišljen je 90-minutni nastavni sat koji se temelji na pokusu i metodi učenja otkrivanjem u kojoj učenici uz nastavnikovu pomoć i pripadajuće nastavne materijale usvajaju nova znanja o kemiji alkina.
Abstract (english)
In this diploma thesis preparation of lipophilic aliphatic azides (dodecyl, hexadecyl) and cholesterol azide was described. Prepared azides were further used as precursors in synthesis of 1,4-disubstitued triazole derivatives. Aliphatic azides were prepared by substitution from the corresponding alkyl bromides and sodium azide. Cholesterol azide was prepared from mesylate derivative. All azides as well as previously prepared 2-(adamantan-1-yl)ethyl azide were transformed into 1,4-disubstitued 1,2,3-triazoles using copper(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) with commercially available propargylamine. di-tert-butyl dicarbonate (Boc2O) was also used in click reaction in order to protect amino group of propargylamine in the same step. Boc group removal with trifluoroacetic acid was carried out next and target molecules, the triazole derivatives of propargylamine, were obtained. The structures of all prepared compounds were confirmed using standard analytical methods - NMR spectroscopy (1H and 13C), infrared spectroscopy (IR) and mass spectrometry (MS). In methodical part was given the comparison of old and new chemistry syllabus and textbooks concerning alkyne chemistry in elementary and high school. A 90-minute lesson based on experiment and inquiry learning was proposed in which students, with help from teacher and accompanying teaching materials, acquire new knowledge about alkyne chemistry.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:036634
Study programmeTitle: Integrated undergraduate and graduate university study of Biology and Chemistry Education; specializations in: Integrated undergraduate and graduate university study of Biology and Chemistry Education
Course: Integrated undergraduate and graduate university study of Biology and Chemistry Education
Study programme type: university
Study level: integrated undergraduate and graduate
Academic / professional title: magistar/magistra edukacije biologije i kemije (magistar/magistra edukacije biologije i kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2022-09-30
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Created on2020-10-27 08:34:25