Naslov
Halogen-bonded Cocrystals of N-salicylidene Schiff Bases and Iodoperfluorinated Benzenes

Autori
Vitković, Matea ; Carletta, Andrea ; Zbačnik, Marija ; Tumay, Nikolay ; Stilinović, Vladimir ; Wouters, Johan ; Cinčić, Dominik

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
II. simpozij supramolekulske kemije : Knjiga sažetaka / Frkanec, Leo ; Namjesnik, Danijel ; Tomišić, Vladislav - Zagreb : Institut Ruđer Bošković, 2018, 21-21

ISBN
978-953-7941-26-0

Skup
2. simpozij supramolekulske kemije

Mjesto i datum
Zagreb, Hrvatska, 12.12.2018

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
halogen bond ; cocrystal ; Schiff base

Sažetak
Halogen bonds are non-covalent interactions formed between polarizable and electron- deficient halogen atoms and electron-rich Lewis bases. Compared to hydrogen bonding, halogen bonds tend to be much more directional and their strength can be easily tuned by the choice of the halogen atom. The study of halogen-bonded multicomponent solids plays significant role in crystal engineering due to ability to obtain new materials with tuneable physical and chemical properties. Recently, Schiff bases have drawn attention as building blocks in such materials due to easy preparation of the molecules with different supramolecular bonding capabilities. In our earlier studies we have reported halogen-bonded cocrystals of Schiff bases derived from o- vanillin where we have demonstrated the halogen bond acceptor potential of methoxy and hydroxy groups via bifurcated I(···O)2 halogen bond motif. In this work we prepared two Schiff bases derived from salicylaldehyde and two amines: aniline (I) and 3- aminopyridine (II) in order to provide insight into the halogen bond acceptor potential of an isolated hydroxyl oxygen of salicylaldehyde moiety in the absence or presence of a potentially competing halogen bond acceptor, pyridine nitrogen (II). For cocrystal screening, as halogen bond donors, we used perfluorinated iodobenzenes: 1, 2-, 1, 3-, 1, 4-diiodotetrafluoro-benzene (12tfib, 13tfib, and 14tfib) and 1, 3, 5- triiodotrifluorobenzene (135tfib). Six cocrystals were obtained by mechanochemical synthesis, while the solution- based method resulted in five single crystals suitable for structure determination. The hydroxyl group has been found to act as a halogen bond acceptor, together with pyridine nitrogen atom in three out of five crystal structures: (II) (13tfib), (II)(135tfib) and (II)2(135tfib), whereas the only cocrystal of I which has been obtained, (I)(14tfib), does not exhibit a halogen bond involving a hydroxyl oxygen.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA