Naslov
Halogen bonded cocrystals of N-bromophthalimide with pyridine derivatives

Autori
Eraković, Mihael ; Lež, Tomislav ; Porupski, Ivan ; Nemec, Vinko ; Stilinović, Vladimir ; Cinčić, Dominik

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

Izvornik
The Twenty-fourth Croatian-Slovenian Crystallographic Meeting - Book of Abstracts / Bijelić, Mirjana ; Cetina, Mario ; Čobić, Andrea ; Matković-Čalogović, Dubravka ; Popović, Stanko ; Štefanić, Zoran ; Tonejc, Antun ; Višnjevac Aleksandar - Zagreb : Hrvatska akademija znanosti i umjetnosti (HAZU) ; Hrvatska kristalografska zajednica HAZU, 2016, 75-75

Skup
The Twenty-fourth Croatian-Slovenian Crystallographic Meeting

Mjesto i datum
Bol, Hrvatska, 22.09.2016. - 24.09.2016

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Nije recenziran

Ključne riječi
N-bromophthalimide ; cocrystals ; halogen bond ; mechanochemistry ; pyridine derivatives

Sažetak
N-haloimides are commercially available compounds commonly used as halogenation agents in organic synthesis. As the halogen atoms in these molecules are extremely polarised, they are potentially extremely strong halogen bond donors, (Raatikainen and Rissanen, 2011 ; Mavračić et al., 2016). Also, they are potentially strong hydrogen bond acceptors considering that they possess carbonyl groups. In this work we have demonstrated how N-bromophthalimide (nbp) can be used in cocrystal synthesis. To the best of our knowledge, we report the first known cocrystals of nbp prepared by both mechanochemical synthesis (liquid-assisted grinding) and conventional solution-based method. As halogen bond acceptors we have used pyridine derivatives with a wide range of nitrogen atom basicity (pKa from 1.4 to 7.5) containing additional functional groups which may be hydrogen bond donors or acceptors. In the crystal structures of all 10 cocrystals molecules are connected via Br∙∙∙N halogen bonds between nbp bromine and pyridine nitrogen atoms. The Br∙∙∙N distances range from 2.38 Å to 2.51 Å and are considerably shorter than the sum of the van der Waals radii (3.4 Å). For all cocrystals the N–Br bond in nbp molecules is extended in comparison to that observed for the pure nbp crystal (up to 0.1 Å) which indicates charge transfer in complexes and partially covalent character of the halogen bond. All supramolecular complexes nbp-pyridine are connected into a 2D or 3D network via C–H∙∙∙O hydrogen bonds between pyridine aromatic rings and carbonyl oxygen atoms of nbp.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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