Co-crystals of iodopentafluorobenzene with nitrogen donors: 2-D molecular assemblies through halogen bonding and aryl–perfluoroaryl interactions

Wasilewska, Aleksandra; Gdaniec, Мaria; Połoński, Tadeusz

doi:10.1039/b617929k

Cited by 34 publications

(31 citation statements)

References 22 publications

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“…Iodopentafluorobenzene (IPFB) is one the most representative compounds of the class of “minimal” XB donors. IPFB gives dimers with 2,6-dimethylpyridine ( Figure 64 , LEZPOW) and 2,4,6-trimethylpyridine 538 (LEZPIQ), and in both cases, the activated iodine atom acts as a powerful XB donor and short contacts are formed. Trimethylpyridine gives a shorter contact than dimethylpyridine as the extra methyl group further activates the electron donor ability of the nitrogen and the presence of a tweezer motif due to HBs between the hydrogen atoms on the 2,6-methyl groups and the negative belt on the iodine atom further promotes the reduction of the donor–acceptor distance.…”

Section: Crystal Engineeringmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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The halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

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Section: Crystal Engineeringmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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“…Indeed, most of the energetic and structural features found in hydrogen‐bonded complexes are reproduced in halogen‐bonded complexes as well. Owing to its strength, selectivity, and directivity, halogen bonding has led to a number of applications in fields, as diverse as molecular recognition, enantiomers's separation, crystal engineering, and supramolecular architectures 2–28. In particular, the utilization of this specific interaction in the context of drug design is nowadays coming to light clearly 3, 29–35.…”

Section: Introductionmentioning

confidence: 99%

Ab initio calculations on halogen‐bonded complexes and comparison with density functional methods

Zou

Fan

et al. 2008

J Comput Chem

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A systematic theoretical investigation on a series of dimeric complexes formed between some halocarbon molecules and electron donors has been carried out by employing both ab initio and density functional methods. Full geometry optimizations are performed at the Moller-Plesset second-order perturbation (MP2) level of theory with the Dunning's correlation-consistent basis set, aug-cc-pVDZ. Binding energies are extrapolated to the complete basis set (CBS) limit by means of two most commonly used extrapolation methods and the aug-cc-pVXZ (X = D, T, Q) basis sets series. The coupled cluster with single, double, and noniterative triple excitations [CCSD(T)] correction term, determined as a difference between CCSD(T) and MP2 binding energies, is estimated with the aug-cc-pVDZ basis set. In general, the inclusion of higher-order electron correlation effects leads to a repulsive correction with respect to those predicted at the MP2 level. The calculations described herein have shown that the CCSD(T) CBS limits yield binding energies with a range of -0.89 to -4.38 kcal/mol for the halogen-bonded complexes under study. The performance of several density functional theory (DFT) methods has been evaluated comparing the results with those obtained from MP2 and CCSD(T). It is shown that PBEKCIS, B97-1, and MPWLYP functionals provide accuracies close to the computationally very expensive ab initio methods.

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“…19 The few examples of formation of discrete adducts are obtained from simple and monodentate tectons. 25 In this study we demonstrate that the careful design of interacting 20 tectons can produce the desired discrete heteromeric capsule, driven by four I···N XBs. 2B is the first halogen-bonded capsule reported to date and its structural similarity with some hydrogen-bonded heteromeric capsules …”

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“…For this reason, we decided to 25 pursue the tetra(3-pyridyl)cavitand 2, which, thanks to the meta orientation of the pyridyl nitrogen atoms, is potentially better suited as a XB-acceptor platform for the assembly of a molecular capsule. On the other hand, even if all of the pyridyl nitrogen atoms 30 of 2 were conveniently oriented in a convergent manner, a linear bridging molecule is not inherently tailored to fulfil the specific geometric requirements associated with the formation of a discrete heteromeric capsule.…”

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confidence: 99%

“…[1][2][3][4][5] The motivation for synthesizing architectures with well-defined and accessible inner cavities is driven by a need to achieve selective encapsulation of molecular guests of different shapes, sizes, and chemical characteristics. 6 Such assemblies can be used 25 for chemical separation 7 and gas encapsulation, 8 as reaction chambers 1a and chiral receptors, in catalysis, social isomerization, 9 and drug-delivery. Covalent interactions, which tend to produce very rigid systems, 6,8-10 metal-ligand interactions, 11,12 and hydrophobic effects, 13 have been used for 30 capsule construction.…”

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The quest for a molecular capsule assembled via halogen bonds

et al. 2012

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A halogen-bonded capsule is obtained via directed assembly of a rigid tetra(3-pyridyl) cavitand and a flexible tetra(4-iodotetrafluorophenyl)calix[4] arene. The pyridyl nitrogen atoms from one cavitand molecule interact with the iodine atoms of a single calixarene molecule through short and directional I⋯N halogen bonds. The flexibility of the ethylenedioxy moieties on the calixarene platform results in positional flexibility of the iodotetrafluorobenzene sites which, coupled with a supramolecular chelating effect, allow for an effective partner-induced geometric fitting between four nitrogen atoms on the cavitand and four iodine atoms on the calixarene

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Co-crystals of iodopentafluorobenzene with nitrogen donors: 2-D molecular assemblies through halogen bonding and aryl–perfluoroaryl interactions

Abstract: Electron deficient iodopentafluorobenzene forms heterodimers with electron rich pyridine donors stabilized by halogen bonding, that are further assembled into polar brick-wall type 2-D network via p-p stacking interactions between aryl and perfluoroaryl moieties.

Cited by 34 publications

References 22 publications

The Halogen Bond

The Halogen Bond

Ab initio calculations on halogen‐bonded complexes and comparison with density functional methods

The quest for a molecular capsule assembled via halogen bonds

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