Naslov
The sulfur atom as a halogen bond acceptor in cocrystals of tetrahydro-4H-thiopyran-4-one and its derivatives

Autori
Nemec, Vinko ; Cinčić, Dominik

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

Izvornik
27th Croatian Meeting of Chemists and Chemical Engineers : Book of Abstracts / Marković, Dean ; Meštrović, Ernest ; Namjesnik, Danijel ; Tomašić, Vesna - Zagreb : Hrvatsko kemijsko društvo, 2021, 131-131

Skup
27. hrvatski skup kemičara i kemijskih inženjera (27HSKIKI)

Mjesto i datum
Veli Lošinj, Hrvatska, 05.10.2021. - 08.10.2021

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
cocrystals, halogen bond, imines, morpholinyl fragment, sp3 sulfur

Sažetak
In the field of crystal engineering by using halogen bonds, sulfur is significantly less studied as an acceptor species relative to the oxygen or nitrogen atoms [1]. An interesting approach in the past two decades was the utilization of the sp3 hybridized sulfur atoms in 1, 4-dithiane, 1, 4-thioxane and thiomorpholine as halogen bond acceptors, whether in binary cocrystals [2] or metal complex adduct cocrystals [3]. In order to further study sp3 hybridized sulfur as a halogen bond acceptor, we have selected tetrahydro-4H-thiopyran-4-one (tpyr), and building blocks derived from it, tpyram and tpyraem, which are obtained by reacting it with 4- aminomorpholine (am) or 4-(2-aminoethyl)morpholine (aem), respectively. All three compounds were then cocrystallized with a series of perhalogenated benzenes: 1, 4-diiodotetrafluorobenzene, 1, 3- diiodotetrafluorobenzene, 1, 2- diiodotetrafluorobenzene, iodopentafluorobenzene, 1, 3, 5-triiodotrifluorobenzene and 1, 4- dibromotetrafluorobenzene, resulting in the formation of 9 new products. Out of these, single crystals were obtained for 7 new products, and they were structurally characterized by X-ray diffraction. Halogen∙∙∙sulfur halogen bonds were formed in 5 out of the 7 cases, the sulfur atom competing for halogen bonding not only with the carbonyl or morpholinyl fragment oxygen atoms, but also with the morpholinyl and imine nitrogen atoms.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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