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

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

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.

langue originaleAnglais
Pages (de - à)5332-5339
Nombre de pages8
journalCrystEngComm
Volume20
Numéro de publication36
Les DOIs
étatPublié - 1 janv. 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. Dans: CrystEngComm. 2018 ; Vol 20, Numéro 36. p. 5332-5339.
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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.",
author = "Andrea Carletta and Marija Zbačnik and Matea Vitković and Nikolay Tumanov and Vladimir Stilinović and Johan Wouters and Dominik Cinčić",
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month = "1",
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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.

Dans: CrystEngComm, Vol 20, Numéro 36, 01.01.2018, p. 5332-5339.

Résultats de recherche: Contribution à un journal/une revueArticle

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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U2 - 10.1039/c8ce01145a

DO - 10.1039/c8ce01145a

M3 - Article

AN - SCOPUS:85053547773

VL - 20

SP - 5332

EP - 5339

JO - CrystEngComm

JF - CrystEngComm

SN - 1466-8033

IS - 36

ER -