Competition and cooperation: hydrogen and halogen bonding in co-crystals involving 4-iodotetrafluorobenzoic acid, 4-iodotetrafluorophenol and 4-bromotetrafluorophenol

Takemura, Akihiro; McAllister, Linda J.; Karadakov, Peter B.; Pridmore, Natalie E.; Whitwood, Adrian C.; Bruce, Duncan W.

doi:10.1039/c4ce00319e

Cited by 34 publications

(26 citation statements)

References 25 publications

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“…2). The 4-iodotetrafluorobenzene is a well known XB donor and thanks to its efficiency in forming very short and directional XBs it has been widely used to promote the construction of a great variety of halogen-bonding complexes (Baldrighi et al, 2010;Aakerö y et al, 2007;Takemura et al, 2014). In addition, 4-iodotetrafluorobenzene can be easily functionalized with different organic pendants without using complex synthetic procedures (Dumele et al, 2015;Bruce et al, 2010).…”

Section: Resultsmentioning

confidence: 99%

“…Although it is known that neutral S atoms may act as good XB acceptors, structures assembled through an SÁ Á ÁI synthon, in which the S atom is in a disulfide bridge, are rare and only a few examples are reported in the Cambridge Structural Database [CSD codes: XESTIZ (Takemura et al, 2014), IFOSUL (Bjorvatten et al, 1962), IFOSUL01 (Wolstenholme et al, 2006) and NEPJIB (Makarov et al, 2001)]. In addition, in these crystal structures the XBs are weak, namely long, with C-IÁ Á ÁS angles quite far away from linearity.…”

Section: Resultsmentioning

confidence: 99%

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Crystallographic insights into the structural aspects of thioctic acid based halogen-bond donor for the functionalization of gold nanoparticles

Sanjeeva

Tirotta

Kumar

et al. 2017

Acta Crystallogr Sect B

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The synthesis and self-assembly capabilities of a new halogen-bond donor ligand, 2,3,5,6-tetrafluoro-4-iodophenyl 5-(1,2-dithiolan-3-yl)pentanoate (1), are reported. The crystal structure of ligand (1) and the formation of a cocrystal with 1,2-di(4-pyridyl)ethylene, (1)·(2), both show halogen bonds involving the 4-iodotetrafluorobenzene moiety. Ligand (1), being a self-complementary unit, forms an infinite halogen-bonded chain driven by the S...I synthon, while the cocrystal (1)·(2) self-assembles into a discrete trimeric entity driven by the N...I synthon. Ligand (1) was also successfully used to functionalize the surface of gold nanoparticles, AuNP-(1). Experiments on the dispersibility profile of AuNP-(1) demonstrated the potential of halogen bonding in facilitating the dispersion of modified NPs with halogen-bond donors in pyridine.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Crystallographic insights into the structural aspects of thioctic acid based halogen-bond donor for the functionalization of gold nanoparticles

Sanjeeva

Tirotta

Kumar

et al. 2017

Acta Crystallogr Sect B

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“…[29,30] By combining interactions that do not compete for the same binding sites, it is, in principle, possible to avoid or at least minimize ''synthon cross-over'', [31] thereby producing architectures of considerable complexity. [34][35][36][37][38][39][40][41][42][43] This is not only because HBs and XBs are similar in strength and properties, but also they are widely applicable to biochemistry and drug design. [33] There are many studies on the competition between various interactions, especially the competition between hydrogen and halogen bonds.…”

Section: Introductionmentioning

confidence: 99%

“…[33] There are many studies on the competition between various interactions, especially the competition between hydrogen and halogen bonds. [34][35][36][37][38][39][40][41][42][43] This is not only because HBs and XBs are similar in strength and properties, but also they are widely applicable to biochemistry and drug design. Alkorta et al studied HBs and XBs formed between hypohalous acid and three nitrogen-containing bases .…”

Section: Introductionmentioning

confidence: 99%

Tuning the Competition between Hydrogen and Tetrel Bonds by a Magnesium Bond

2020

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A computational study of the complexes formed by TF 3 OH (T=C, Si, Ge) with three nitrogen-containing bases NCH, NH 3 , and imidazole (IM) is carried out at the MP2/aug-cc-pVTZ level. TF 3 OH can participate in two different types of noncovalent interactions: a hydrogen bond (HB) involving the hydroxyl proton and a tetrel bond (TB) with the tetel atom T. The strength of the HB is largely unaffected by the identity of T while the TB is enhanced as T grows larger. The HB is preferred over the TB for most systems, with the exception of GeF 3 OH with either NH 3 or IM. MgCl 2 engages in a Mg···O Magnesium bond (Mg-bond) with the TF 3 OH O atom, which cooperatively enhances both the HB and TB. The HB strengthening is particularly large for the NH 3 or IM bases, and especially for CF 3 OH, but is slowly reduced as the T atom grows larger. The TB enhancement, on the other hand, behaves in the opposite fashion, accelerating for the larger T atoms. As a bottom line, the Mg-bond generally reinforces and accentuates the preference for the HB or TB that is already present in the dimer. The Mg-bond is also responsible for a proton transfer in the HB configurations with NH 3 and IM.[a] Dr.

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“…As a result, the directed assembly of compositionally and structurally complex architectures requires a thorough understanding of the way in which complementary and competing forces eventually lead to a stable solid-state architecture [6,7]. Against this background, our goal was to establish reliable and robust avenues for the design and synthesis of crystalline metal-containing materials by encoding each building-block with structural-preferences that lead to "programmable" and predictable assembly [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

The Role of Halogen Bonding in Controlling Assembly and Organization of Cu(II)-Acac Based Coordination Complexes

et al. 2017

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Abstract:In order to explore the use of non-covalent interactions in the deliberate assembly of metal-supramolecular architectures, a series of β-diketone based ligands capable of simultaneously acting as halogen-bond donors and chelating ligands were synthesized. The three ligands, L1, L2, and L3, carry ethynyl-activated chlorine, bromine, and iodine atoms, respectively and copper(II) complexes of all three ligands were crystallized from different solvents, acetonitrile, ethyl acetate, and nitromethane in order to study specific ligand-solvent interaction. The free ligands L2 and L3, with more polarizable halogen atoms, display C-X· · · O halogen bonds in the solid state, whereas the chloro-analogue (L1) does not engage in halogen bonding. Both acetonitrile and ethyl acetate act as halogen-bond acceptors in Cu(II)-complexes of L2 and L3 whereas nitromethane is present as a 'space-filling' guest without participating in any significant intermolecular interactions in Cu(II)-complexes of L2. L3, which is decorated with an iodoethynyl moiety and consistently engages in halogen-bonds with suitable acceptors. This systematic structural analysis allows us to rank the relative importance of a variety of electron-pair donors in these metal complexes.

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Competition and cooperation: hydrogen and halogen bonding in co-crystals involving 4-iodotetrafluorobenzoic acid, 4-iodotetrafluorophenol and 4-bromotetrafluorophenol

Abstract: Careful choice of components can lead to the favouring of halogen over hydrogen bonding.

Cited by 34 publications

References 25 publications

Crystallographic insights into the structural aspects of thioctic acid based halogen-bond donor for the functionalization of gold nanoparticles

Crystallographic insights into the structural aspects of thioctic acid based halogen-bond donor for the functionalization of gold nanoparticles

Tuning the Competition between Hydrogen and Tetrel Bonds by a Magnesium Bond

The Role of Halogen Bonding in Controlling Assembly and Organization of Cu(II)-Acac Based Coordination Complexes

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