Halogen Bonding in Supramolecular Chemistry

Metrangolo, Pierangelo; Meyer, Franck; Pilati, Tullio; Resnati, Giuseppe; Terraneo, Giancarlo

doi:10.1002/anie.200800128

Cited by 1,495 publications

(1,040 citation statements)

References 181 publications

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“…3 and the parameters are given in Table 4. Halogen bonding in general has been of considerable recent interest [5][6][7][8] and such an interaction between bromine and carbonyl oxygen has been studied both computationally [9,10] and experimentally [11] in simple molecules, and by surveying complex biological structures [12]. However the two interactions here show unusual features.…”

Section: Resultsmentioning

confidence: 96%

The X-ray Structures of 2,4-Dibromothiazole and 2,4-Diacetyl-5-bromothiazole

Aitken

MacGregor

et al. 2015

J Chem Crystallogr

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Section: Resultsmentioning

confidence: 96%

The X-ray Structures of 2,4-Dibromothiazole and 2,4-Diacetyl-5-bromothiazole

Aitken

MacGregor

et al. 2015

J Chem Crystallogr

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“…Another possibility for visualizing molecular interactions is the Electron Localization Function (ELF), 160,161 which is a scalar field associated with same-spin pair densities of electrons that is a popular descriptor for accessing both the bonding and atomic shell structure. Unfortunately, while extremely useful for characterizing covalent bonding, ELF only recognizes non-covalent interactions arising from strong electrostatic forces, mainly those occurring in hydrogen bonds, 162,163 halogen bonds, 164,165 and pnicogen bonds. 166 Given that each of the above tools fails to properly describe weak non-covalent interactions, it becomes necessary to search for an alternative approach elsewhere.…”

Section: Visualization Toolsmentioning

confidence: 99%

Perspective: Found in translation: Quantum chemical tools for grasping non-covalent interactions

Pastorczak¹,

Corminbœuf²

2017

The Journal of Chemical Physics

103

102

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Today's quantum chemistry methods are extremely powerful but rely upon complex quantities such as the massively multidimensional wavefunction or even the simpler electron density. Consequently, chemical insight and a chemist's intuition are often lost in this complexity leaving the results obtained difficult to rationalize. To handle this overabundance of information, computational chemists have developed tools and methodologies that assist in composing a more intuitive picture that permits better understanding of the intricacies of chemical behavior. In particular, the fundamental comprehension of phenomena governed by non-covalent interactions is not easily achieved in terms of either the total wavefunction or the total electron density, but can be accomplished using more informative quantities. This perspective provides an overview of these tools and methods that have been specifically developed or used to analyze, identify, quantify, and visualize non-covalent interactions. These include the quantitative energy decomposition analysis schemes and the more qualitative class of approaches such as the Non-covalent Interaction index, the Density Overlap Region Indicator, or quantum theory of atoms in molecules. Aside from the enhanced knowledge gained from these schemes, their strengths, limitations, as well as a roadmap for expanding their capabilities are emphasized. ©2017Author(s

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“…Among different noncovalent interactions, the halogen bond (X-bond) attracts particular attention of researchers because, similarly as the hydrogen bond (H-bond), it is responsible for physical, chemical, and biologic properties of a large group of chemical species [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. The X-bond is of the strength close to that of H-bond [1] and is strongly directional [17].…”

Section: Introductionmentioning

confidence: 99%

The shape of the halogen atom—anisotropy of electron distribution and its dependence on basis set and method used

Bankiewicz

Palusiak

2012

Struct Chem

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A search through Crystal Structure Database was performed and the distances in contacts of XÁÁÁN,O, XÁÁÁH(N,O), and XÁÁÁC type were collected together with the information on spatial arrangement of the interacting fragments. A detailed statistical analysis showed that the shape of the halogen atom cannot be simply concluded on the basis of interatomic distances in crystal state although originally the concept of anisotropic charge distribution around halogen nuclei was postulated on the basis of such an analysis. It was proven that the conclusions in that case strongly depend on the type of center interacting with the halogen atom. Therefore, it was postulated that the shape of the halogen atom can be estimated for the unperturbed (due to intermolecular interactions) halogen atom. For this purpose, a method was provided to make possible a numerical quantification of the anisotropy of the halogen atom on the basis of electron density measurements performed within the framework of Atoms in Molecules Quantum Theory. The anisotropy of Cl and Br atoms in H 3 C-X and F 3 C-X (X=Cl, Br) was estimated for MP2 and DFT-B3LYP methods and several different basis sets. The influence of the method and the basis set on the degree of anisotropic distribution of electron density around halogen nuclei was discussed.Keywords Halogen bond Á The shape of the atom Á QTAIM Á DFT Á MP2 Á Basis set

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Halogen Bonding in Supramolecular Chemistry

Cited by 1,495 publications

References 181 publications

The X-ray Structures of 2,4-Dibromothiazole and 2,4-Diacetyl-5-bromothiazole

The X-ray Structures of 2,4-Dibromothiazole and 2,4-Diacetyl-5-bromothiazole

Perspective: Found in translation: Quantum chemical tools for grasping non-covalent interactions

The shape of the halogen atom—anisotropy of electron distribution and its dependence on basis set and method used

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