Naslov
Cocrystallization of trimethylphenylammonium iodide with perfluorinated halogen bond donors

Autori
Liović, Marin ; Stilinović, Vladimir ; Cinčić, Dominik

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

Izvornik
27th Slovenian – Croatian Crystallographic Meeting : Book of Abstracts / - , 2019, 55-55

Skup
27th Slovenian-Croatian Crystallographic Meeting (SCCM 2019)

Mjesto i datum
Rogaška Slatina, Slovenija, 19.06.2019. - 23.06.2019

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
cocrystallization ; halogen bond

Sažetak
Halogen bond is a directional noncovalent interaction that plays a significant role in crystal packing. Interaction is achieved between a positive o-hole on a halogen atom covalently bonded to an electron-withdrawing group (halogen bond donor), and a Lewis base (halogen bond acceptor). With regard to the wide spectrum of Lewis bases studied to date, halogenide ions are poorly investigated halogen bond acceptors [1], [2]. In this study, with the aim of studying halogen bonded motifs by sterically differing the cation, we attempted to prepare the series of cocrystals of trimethylphenylammonium iodide (MeaPhNHI) with perfluorinated halogen bond donors: 1, 4- diiodooctafluorobutane (ofib), 1, 4- diiodotetrafluorobenzene (14tfib) and 1, 3, 5- triiodotrifluorobenzene (135titfb), respectively. Me3PhNHI was prepared by isolating the precipitate formed by heating the solution of dimethylphenylamine in iodomethane under reflux. Three cocrystals of different stoichiometries were obtained by dissolving Me3PhNHI and halogen bond donors in ethanol: (Me3PhNHI)2(ofib), (Me3PhNHI)2(14tfib)3, and (Me3PhNHI)3(135titfb)2. In all prepared cocrystals, halogen bond donors and iodide ions form C–I⋯I− halogen bonds, F forming a different number of halogen bonds in each one. Although both ofib and 14tfib are linear ditopic donors, they yielded quite dissimilar halogen bonded structures - ofib forms discrete I−⋯ofib⋯I− trimers, whereas 14tfib forms 2D- sheets where the iodide ion acts as a tritopic acceptor with nearly trigonal geometry. Similar to 14tfib, 135titfb forms 2D-sheets. Here, however, 135titfb is a tritopic donor with iodide ion as a nearly linear ditopic acceptor. This demonstrates considerable flexibility of the iodide ion as an acceptor, both in its topicity and coordination geometry, which is of great potential interest for crystal engineering of organic halide cocrystals.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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