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master's thesis
Utjecaj supstituenata na nukleofilnost purinskih baza
Zagreb: University of Zagreb, Faculty of Pharmacy and Biochemistry, 2023. urn:nbn:hr:163:587344
Simić, Marin
University of Zagreb
Faculty of Pharmacy and Biochemistry
Department of organic chemistry

Institutional repository: Repository of Faculty of Pharmacy and Biochemistry University of Zagreb

Cite this document

Simić, M. (2023). Utjecaj supstituenata na nukleofilnost purinskih baza (Master's thesis). Zagreb: University of Zagreb, Faculty of Pharmacy and Biochemistry. Retrieved from https://urn.nsk.hr/urn:nbn:hr:163:587344

Simić, Marin. "Utjecaj supstituenata na nukleofilnost purinskih baza." Master's thesis, University of Zagreb, Faculty of Pharmacy and Biochemistry, 2023. https://urn.nsk.hr/urn:nbn:hr:163:587344

Simić, Marin. "Utjecaj supstituenata na nukleofilnost purinskih baza." Master's thesis, University of Zagreb, Faculty of Pharmacy and Biochemistry, 2023. https://urn.nsk.hr/urn:nbn:hr:163:587344

Simić, M. (2023). 'Utjecaj supstituenata na nukleofilnost purinskih baza', Master's thesis, University of Zagreb, Faculty of Pharmacy and Biochemistry, accessed 26 November 2024, https://urn.nsk.hr/urn:nbn:hr:163:587344

Simić M. Utjecaj supstituenata na nukleofilnost purinskih baza [Master's thesis]. Zagreb: University of Zagreb, Faculty of Pharmacy and Biochemistry; 2023 [cited 2024 November 26] Available at: https://urn.nsk.hr/urn:nbn:hr:163:587344

M. Simić, "Utjecaj supstituenata na nukleofilnost purinskih baza", Master's thesis, University of Zagreb, Faculty of Pharmacy and Biochemistry, Zagreb, 2023. Available at: https://urn.nsk.hr/urn:nbn:hr:163:587344

Metadata
TitleUtjecaj supstituenata na nukleofilnost purinskih baza
Title (english)The influence of substituents on the nucleophilicity of purine bases
AuthorMarin Simić
MentorValerije Vrček (mentor)
Committee memberValerije Vrček (predsjednik povjerenstva)
Committee memberTin Weitner (član povjerenstva)
Committee memberDavor Šakić (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Pharmacy and Biochemistry
(Department of organic chemistry)
Zagreb
Defense date and country2023-06-13, Croatia
Scientific / art field,
discipline and subdiscipline		BIOMEDICINE AND HEALTHCARE
Pharmacy
Pharmacy
Abstract
Kvantno-kemijskim metodama izračunate su kondenzirane Fukui funkcije za purin, adenin i derivate adenina, te je provedena usporedba s prethodno poznatim eksperimentalnim rezultatima konjugacije ferocenoil-klorida na purin i njegove derivate. SN2-slična supstitucijska reakcija između ferocenoilklorida i aniona adenina je regioselektivan proces u kojem omjer produkata (N7/N9-ferocenoil izomera) ovisi o steričkim svojstvima supstituenta na N6-položaju. Veliki, razgranati supstituenti na N6-atomu mogu ometati reakciju na N7-položaju, sprječavajući pristup elektrofila. Kao posljedica toga, smanjuje se udio N7-produkta, tj. raste udio N9-ferocenoil regioizomera. U slučaju kad je sterički učinak zanemariv, kao npr. kod purina, prevladava elektronski učinak N6-supstituenta, što je potkrijepljeno izračunima kondenziranih Fukui funkcija. Svi izračuni pokazuju da je atom N7 nukleofilniji od N9-atoma u svim purinskim derivatima.
Abstract (english)
Condensed Fukui functions for purine, adenine and adenine derivatives were calculated using quantum chemical methods and a comparison was made with previously known experimental results of ferrocenyl chloride conjugation to purine and its derivatives. The SN2-like substitution reaction between ferrocenoyl chloride and adenine anion is a regioselective process in which the product ratio (N7/N9-ferrocenoyl isomer) depends on the steric properties of the substituent at the N6- position. Large, bulky substituents at the N6-atom can hinder the reaction at the N7-position, preventing access of an electrophile. As a consequence, the proportion of N7-product decreases, i.e. the proportion of N9-ferrocenoyl regioisomer increases. In the case when the steric effect is negligible, such as for purines, the electronic effect of the N6-substituent prevails, which is supported by calculations of condensed Fukui functions. All calculations show that the N7 atom is more nucleophilic than the N9 atom in all purine derivatives.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:163:587344
Study programmeTitle: Pharmacy
Study programme type: university
Study level: integrated undergraduate and graduate
Academic / professional title: magistar/magistra farmacije (magistar/magistra farmacije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2024-01-04 16:02:10