Cocrystallization of 3,5-dibromopyridinium chloride with perhalogenated halogen bond donors

U sklopu ovog diplomskog rada pripravljena je kloridna sol 3,5-dibrompiridina. Mehanokemijskom sintezom i kristalizacijom iz otopine izučavana je mogućnost nastajanja kokristala pripravljene soli s odabranim perhalogeniranim donorima halogenske veze: oktafluor-1,4-dijodbutanom, heptadekafluor-1-jodoktanom, pentafluorjodbenzenom, tetrafluor-1,2-dijodbenzenom, tetrafluor-1,3-dijodbenzenom, tetrafluor-1,4-dijodbenzenom i trifluor-1,3,5-trijodbenzenom. Pripravljeni spojevi izučavani su razlikovnom pretražnom kalorimetrijom, metodom difrakcije rentgenskih zraka na praškastom uzorku i metodom difrakcije rentgenskih zraka na jediničnom kristalu. Za tri pripravljena kokristala je metodom rentgenske difrakcije na jediničnom kristalu određena molekulska i kristalna struktura. U svim kokristalima kloridni anion akceptor je halogenske veze I···Cl− i vodikove veze N−H···Cl−, dok njegova koordinacijska sfera i supramolekulska arhitektura ovise o korištenim donorima.Within this master thesis a chloride salt of 3,5-dibromopyridine was prepared. Mechanochemical synthesis and crystallization from solution were used to study cocrystal formation with the chosen halogen bond donors: octafluoro-1,4-diiodobutane, heptadecafluoro-1-iodooctane, pentafluoroiodobenzene tetrafluoro-1,2-diiodobenzene, tetrafluoro-1,3-diiodobenzene, tetrafluoro-1,4-diiodobenzene and trifluoro-1,3,5- triiodobenzene. Prepared cocrystals were analyzed by differential scanning calorimetry, powder X-ray diffraction and single crystal X-ray diffraction. Three cocrystals were prepared and their molecular and crystal structures determined. In all cases, the chloride ion was the main acceptor of the I···Cl− halogen bond and the N−H···Cl− hydrogen bond. The chloride ion coordination sphere as well as the supramolecular arhitecture found in the prepared cocrystals depended on the halogen bond donor used