Naslov
1,3- and 1,4-diiodotetrafluorobenzene as halogen bond donors in crystal engineering

Autori
Bedeković, Nikola ; Stilinović, Vladimir ; Friščić, Tomislav ; Cinčić, Dominik

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

Izvornik
25th Congress of Chemists and Technologists of Macedonia : Book of Abstracts / Stafilov, Trajče ; Petreska Stanoeva, Jasmina - Skopje : Society of Chemists and Technologists of Macedonia, 2018, 249-249

ISBN
978-9989-760-16-7

Skup
25th Congress of Chemists and Technologists of Macedonia (SCTM 2018)

Mjesto i datum
Ohrid, Sjeverna Makedonija, 19.09.2018. - 22.09.2018

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
halogen bonding ; crystal engineering ; cocrystals

Sažetak
Halogen bond (XB) is an attractive, strong and directional noncovalent interaction between chemical entity with usually covalently bonded and partially positively charged halogen atom (halogen bond donor) and some Lewis base.1 This interaction has attracted considerable attention in the solid state chemistry, where it is widely used for the synthesis of the new materials. The most usual halogen bond donors in solid state chemistry are perhalogenated hydrocarbons, of which 1, 4-diiodotetrafluorobenzene (1, 4-tfib) is probably the most extensively used halogen bond donor to date, while 1, 3-diiodotetrafluorobenzene (1, 3-tfib) has remained almost completely unexplored (18 crystal structures in CSD).2 This study investigates the structures of 14 new cocrystals of the bent 1, 3-diiodotetrafluorobenzene and 9 new, analogous cocrystals of linear 1, 4-diiodotetrafluorobenzene, with 9 monotopic and 7 ditopic nitrogen-based aliphatic and aromatic halogen bond acceptors. In particular, whereas our comparative study of 1, 3-tfib and 1, 4-tfib cocrystals with used halogen bond acceptors reveals a similarity in I···N halogen bond lengths and distribution of melting points of explored cocrystals, it also reveals differences in stoichiometric compositions of cocrystals and the structures of underlying halogen-bonded motifs. Tentatively, the herein observed differences in halogen-bonded motifs and cocrystal composition are explained through changes in the efficiency of crystal packing upon switching from a linear halogen bond donor to the bent 1, 3-tfib. This implies that, at least in some cases, close packing, rather than halogen bonding strength may be the force that determines the supramolecular architecture and stoichiometric composition of the final the product.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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