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Halogen-bonded cocrystals of N-salicylidene Schiff bases and iodoperfluorinated benzenes: hydroxyl oxygen as halogen bond acceptor

Abstract

To explore the halogen bonding proclivity of the o-hydroxyimine hydroxyl group, we have prepared two imines as halogen bond acceptors: salicylideneaniline (I) and a 3-pyridyl analogue (II) derived by condensation of salicylaldehyde and 3-aminopyridine. These two Schiff bases were selected as two simplest representatives of o-hydroxyimines, where one (II) possesses a potentially competing halogen bond acceptor (pyridine nitrogen), and the other does not. For cocrystal screening, as halogen bond donors we used perfluorinated iodobenzenes: 1,2-, 1,3-, 1,4-diiodotetrafluoro-benzene (12tfib, 13tfib, 14tfib) and 1,3,5-triiodotrifluoro-benzene (135tfib). The hydroxyl group has been found to act as a halogen bond acceptor in three out of five crystal structures determined in this study: (II)(13tfib), (II)(135tfib) and (II)2(135tfib). In all three cases a pyridine nitrogen is also employed in halogen bonding. Our attempts of preparing cocrystals of I were generally unsuccessful and the only cocrystal of I which has been obtained, with 14tfib, does not exhibit a halogen bond involving a hydroxyl oxygen. These results suggest that halogen bond motif with an isolated hydroxyl group as acceptor seems to be less favourable than previousely studied bifurcated halogen bonding motif with the ortho-methoxy-hydroxy group as acceptor.

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Publication details

The article was received on 12 Jul 2018, accepted on 01 Aug 2018 and first published on 02 Aug 2018


Article type: Paper
DOI: 10.1039/C8CE01145A
Citation: CrystEngComm, 2018, Accepted Manuscript
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    Halogen-bonded cocrystals of N-salicylidene Schiff bases and iodoperfluorinated benzenes: hydroxyl oxygen as halogen bond acceptor

    A. Carletta, M. Zbačnik, M. Vitković, N. Tumanov, V. Stilinovic, J. Wouters and D. Cinčić, CrystEngComm, 2018, Accepted Manuscript , DOI: 10.1039/C8CE01145A

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