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doctoral thesis
Halogenpiridinijevi kvarterni kationi kao donori halogenske veze
Zagreb: University of Zagreb, Faculty of Science, 2022. urn:nbn:hr:217:996672
Fotović, Luka
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

Cite this document

Fotović, L. (2022). Halogenpiridinijevi kvarterni kationi kao donori halogenske veze (Doctoral thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:996672

Fotović, Luka. "Halogenpiridinijevi kvarterni kationi kao donori halogenske veze." Doctoral thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:996672

Fotović, Luka. "Halogenpiridinijevi kvarterni kationi kao donori halogenske veze." Doctoral thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:996672

Fotović, L. (2022). 'Halogenpiridinijevi kvarterni kationi kao donori halogenske veze', Doctoral thesis, University of Zagreb, Faculty of Science, accessed 31 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:996672

Fotović L. Halogenpiridinijevi kvarterni kationi kao donori halogenske veze [Doctoral thesis]. Zagreb: University of Zagreb, Faculty of Science; 2022 [cited 2024 December 31] Available at: https://urn.nsk.hr/urn:nbn:hr:217:996672

L. Fotović, "Halogenpiridinijevi kvarterni kationi kao donori halogenske veze", Doctoral thesis, University of Zagreb, Faculty of Science, Zagreb, 2022. Available at: https://urn.nsk.hr/urn:nbn:hr:217:996672

Metadata
TitleHalogenpiridinijevi kvarterni kationi kao donori halogenske veze
Title (english)Quaternary halogenopyridinium cations as halogen bond donors
AuthorLuka Fotović
MentorVladimir Stilinović (mentor)
Committee memberBiserka Prugovečki (predsjednik povjerenstva)
Committee memberKrešimir Molčanov (član povjerenstva)
Committee memberJosip Požar (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2022-02-18, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Universal decimal classification
(UDC)		54 - Chemistry. Crystallography. Mineralogy
Abstract
U ovome istraživanju, uvođenjem različitih (alifatskih) supstituenata na piridinski dušikov atom halogenpiridina (osobito meta izomera) pripravljeno je te strukturno, termički i spektroskopski okarakterizirano 49 novih soli protoniranih i N-alkiliranih halogenpiridina. Usporedbom halogenskih veza u strukturama N-alkil-3-jodpiridinijevih jodida utvđeno da postoji trend da što je duži ugljikovodični lanac supstituiran na dušikov atom jodpiridinskog prstena to su kraće halogenske veze C−I⋯I−. Ustanovljeno je da afinitet prema halogenskoj vezi opada s veličinom halogenidnog aniona kao akceptora, odnosno slijedi isti trend kao i u slučaju vodikove veze. Analizom raspodjele naboja na halogenpiridinijevim kationima utvrđeno je da i protoniranje i N-metiliranje halogenpiridina dovode do značajnog povećanja elektrostatskog potencijala σšupljine halogena što uvelike povećava incidenciju ostvarivanja halogenskih veza u odnosu na neutralne halogenpiridine. To čini halogenpiridinijeve katione (jodpiridinijeve posebno) prilično pouzdanim donorima halogenskih veza, te na taj način opravdava njihovu upotrebu u dizajnu i sintezi supramolekulskih struktura povezanih halogenskom vezom.
Abstract (english)
In this study, 49 novel salts of halogenopyridinium cations were prepared and characterized by single crystal X-ray diffraction, and by thermal and spectroscopic analysis methods. In the crystal structures of N-alkyl-3-iodopyridinium iodides it is observed trend that longer chains as N-substituents generally leading to shorter C−I⋯I− halogen bonds. Based on the trend observed in the relative shortenings of distances of the two interactions, both halogen and hydrogen bonds seem to be decreasing in strength with the size of the halogenide anion. Inspection of the distribution of the charge on the cations revealed that both protonation and N-methylation of halogenopyridines lead to a considerable increase in the electrostatic potential of the halogen σ-hole which increase incidence of the halogen bond in the structures comprising halogenopyridinium cations (as compared to neutral halogenopyridines). This makes halopyridiniom cations (iodopyridinium in particularly) fairly reliable halogen bond donors for deliberate synthesis of halogen bonded supramolecular structures.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:996672
Promotion2022
ProjectNumber: IP-2014-09-7367
Title: Kristalno inženjerstvo višekomponentinih metaloorganksih materijala povezanih halogenskom vezom: ususret supramolekulskom ugađanju strukture i svojstava
Title: Crystal engineering of multicomponent halogen bonded metal-organic materials: towards supramolecular control over structure and properties
Acronym: CrystEngMOM
Leader: Dominik Cinčić
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
ProjectNumber: 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 programmeTitle: Doctoral study in chemistry
Study programme type: university
Study level: postgraduate
Academic / professional title: doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija (doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija)
Type of resourceText
Extent93 str. ; 30 cm
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2022-02-23 12:18:12