Halogen⋯halogen interactions in diiodo-xylenes

Albright, Emily L.; Cann, Jonathan; Decken, Andreas; Eisler, Sara

doi:10.1039/c6ce02339h

Cited by 13 publications

(13 citation statements)

References 27 publications

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“…With this unique combination of properties halogen bonds enable molecular assemblies with manifold conformations. This is particularly interesting for broad applications in the fields of supramolecular chemistry [1][2][3][4] , crystal engineering [5][6][7] , catalysis 8 , and drug design 9,10 . This potential was gradually realized during the last two decades when the nature of the halogen bond was better understood.…”

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confidence: 99%

Surface-controlled reversal of the selectivity of halogen bonds

et al. 2020

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Intermolecular halogen bonds are ideally suited for designing new molecular assemblies because of their strong directionality and the possibility of tuning the interactions by using different types of halogens or molecular moieties. Due to these unique properties of the halogen bonds, numerous areas of application have recently been identified and are still emerging. Here, we present an approach for controlling the 2D self-assembly process of organic molecules by adsorption to reactive vs. inert metal surfaces. Therewith, the order of halogen bond strengths that is known from gas phase or liquids can be reversed. Our approach relies on adjusting the molecular charge distribution, i.e., the σ-hole, by molecule-substrate interactions. The polarizability of the halogen and the reactiveness of the metal substrate are serving as control parameters. Our results establish the surface as a control knob for tuning molecular assemblies by reversing the selectivity of bonding sites, which is interesting for future applications.

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confidence: 99%

Surface-controlled reversal of the selectivity of halogen bonds

et al. 2020

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“…There are four crystals in this category, three having two iodide substituents in their molecular formula, i.e. 158, 220 159 221 and 160, 222 and one having four substituents, namely 161; 223 see Fig. 14 for chemical diagrams and ESI Table 6 for further details.…”

Section: Two-dimensional Aggregates Sustained By a C-i•••π(arene) Intmentioning

confidence: 99%

“…Each of the molecules accepts and donates two C-I•••π(arene) interactions which extend laterally to form a two-dimensional array, two molecules thick. In the second motif, found in each of 159 221 and 160, 222 one arene ring, located about a centre of inversion, accepts two contacts, one to either side, and each of the iodide atoms participates in a C-I•••π(arene) interaction. Again, these extend laterally to form a twodimensional array as illustrated for 159 221 in Fig.…”

Section: Crystengcomm Accepted Manuscriptmentioning

confidence: 99%

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Supramolecular architectures sustained by delocalised C–I⋯π(arene) interactions in molecular crystals and the propensity of their formation

Tiekink

2021

CrystEngComm

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“…phenol ring interacts with the Cl4 atom of the dichlorophenol ring. The ClÁ Á ÁCl contact can be classified as a Type I halogen bond (1 = 2; where 1 and 2 are the C-ClÁ Á ÁCl angles; Desiraju & Parthasarathy, 1989;Mukherjee & Desiraju, 2014;Albright et al, 2017). 5, 6 and 7; Fig.…”

Section: Figurementioning

confidence: 99%

Role of halogen–halogen contacts in the crystal structures of three new solvates of the drug oxyclozanide

Sridhar

Ravikumar

2017

Acta Crystallogr C

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Halogen-halogen contacts are electrostatic in nature and exhibit directionality similar to hydrogen bonds. Oxyclozanide [systematic name: 2,3,5-trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide] is a drug used for the treatment of fascioliasis in domestic animals. The molecule carries five chlorine substituents and represents an ideal candidate for the study of halogen bonds in the crystal. Three new crystalline solvates of oxyclozanide, namely, oxyclozanide benzene hemisolvate, CHClNO·0.5CH, (I), oxyclozanide xylene hemisolvate, CHClNO·0.5CH, (II), and oxyclozanide toluene hemisolvate, CHClNO·0.5CH, (III), were structurally characterized. In this context, the crystal structure of oxyclozanide chlorobenzene hemisolvate, CHClNO·0.5CHCl, (IV), was redetermined based on intensity data collected at 100 K. In all four solvates, the cocrystallized solvent molecules are located on crystallographic inversion centres. Solvates (I)-(IV) exhibit similar one-dimensional hydrogen-bonded chains generated by O-H...O, O-H...Cl and Cl...Cl interactions. The extension of these one-dimensional chains into two-dimensional layers is promoted by Cl...Cl and C-H...π contacts. Solvates (III) and (IV) are isostructural and differ from (I) and (II) with respect to subtle details concerning the intermolecular contacts.

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Halogen⋯halogen interactions in diiodo-xylenes

Cited by 13 publications

References 27 publications

Surface-controlled reversal of the selectivity of halogen bonds

Surface-controlled reversal of the selectivity of halogen bonds

Supramolecular architectures sustained by delocalised C–I⋯π(arene) interactions in molecular crystals and the propensity of their formation

Role of halogen–halogen contacts in the crystal structures of three new solvates of the drug oxyclozanide

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