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

Andrea Carletta, Marija Zbačnik, Matea Vitković, Nikolay Tumanov, Vladimir Stilinović, Johan Wouters, Dominik Cinčić

Research output: Contribution to journalArticle

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 from the condensation of salicylaldehyde and 3-aminopyridine. These two Schiff bases were selected as the 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, and 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 at 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 the halogen bond motif with an isolated hydroxyl group as the acceptor seems to be less favourable than the previously studied bifurcated halogen bonding motif with the ortho-methoxy-hydroxyl group as the acceptor.

Original languageEnglish
Pages (from-to)5332-5339
Number of pages8
JournalCrystEngComm
Volume20
Issue number36
DOIs
Publication statusPublished - 1 Jan 2018

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Halogens
Schiff Bases
Benzene
Hydroxyl Radical
halogens
imines
benzene
Oxygen
Pyridine
oxygen
Nitrogen
Condensation
Screening
Crystal structure
Iodobenzenes
pyridines
nitrogen
Imines
screening
condensation

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Carletta, Andrea ; Zbačnik, Marija ; Vitković, Matea ; Tumanov, Nikolay ; Stilinović, Vladimir ; Wouters, Johan ; Cinčić, Dominik. / Halogen-bonded cocrystals of N -salicylidene Schiff bases and iodoperfluorinated benzenes: Hydroxyl oxygen as a halogen bond acceptor. In: CrystEngComm. 2018 ; Vol. 20, No. 36. pp. 5332-5339.
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Halogen-bonded cocrystals of N -salicylidene Schiff bases and iodoperfluorinated benzenes: Hydroxyl oxygen as a halogen bond acceptor. / Carletta, Andrea; Zbačnik, Marija; Vitković, Matea; Tumanov, Nikolay; Stilinović, Vladimir; Wouters, Johan; Cinčić, Dominik.

In: CrystEngComm, Vol. 20, No. 36, 01.01.2018, p. 5332-5339.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Halogen-bonded cocrystals of N -salicylidene Schiff bases and iodoperfluorinated benzenes: Hydroxyl oxygen as a halogen bond acceptor

AU - Carletta, Andrea

AU - Zbačnik, Marija

AU - Vitković, Matea

AU - Tumanov, Nikolay

AU - Stilinović, Vladimir

AU - Wouters, Johan

AU - Cinčić, Dominik

PY - 2018/1/1

Y1 - 2018/1/1

N2 - 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 from the condensation of salicylaldehyde and 3-aminopyridine. These two Schiff bases were selected as the 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, and 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 at 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 the halogen bond motif with an isolated hydroxyl group as the acceptor seems to be less favourable than the previously studied bifurcated halogen bonding motif with the ortho-methoxy-hydroxyl group as the acceptor.

AB - 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 from the condensation of salicylaldehyde and 3-aminopyridine. These two Schiff bases were selected as the 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, and 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 at 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 the halogen bond motif with an isolated hydroxyl group as the acceptor seems to be less favourable than the previously studied bifurcated halogen bonding motif with the ortho-methoxy-hydroxyl group as the acceptor.

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DO - 10.1039/c8ce01145a

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