Synthesis, structural characterization, and theoretical analysis of novel zinc(ii ) schiff base complexes with halogen and hydrogen bonding interactions
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Different supramolecular interactions in the solid state structures of three zinc( ii ) Schiff base complexes have been analyzed using DFT calculations and a variety of computational tools (MEP, QTAIM and NCIplot).Keywords:
Halogen bond
Halogen bond
Fluorine
Non-covalent interactions
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Halogen bond
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Weak but measurable: a supramolecular balance detects interactions between CBr3groups in solution and estimates the corresponding free energy (0.2 kJ mol−1).
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Reactions of the uranyl cation (UO22+) with 4-halopyridinium ions (X = Cl, Br, I) in high halide media (X′ = Cl, Br) have produced six novel compounds, the structures of which have been determined by single crystal X-ray diffraction (XRD). The compounds can be divided into two categories based on the different modes of hydrogen bonding and halogen–halogen interactions present in the crystal structures, with one group showing approximately Type I halogen–halogen interactions and the second showing Type II. Presented is a discussion of the relative strengths of the interactions as a function of halogen size.
Halogen bond
Uranyl
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Hydrogen bonding patterns and halogen⋯halogen interactions, C/N–H⋯Cl hydrogen bonding in a series of multi-component molecular structures constructed by tetrachlorophthalic acid with N-heterocycles were discussed.
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Crystal (programming language)
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The term halogen bonding describes the tendency of halogen atoms to interact with lone pair possessing atoms. The binding features and structural properties of halogen bonding are discussed and applied to drive the intermolecular self-assembly of hydrocarbons and perfluorocarbons in chemo-, site-, and enantioselective supramolecular synthesis. The halogen bonding is thus an effective and reliable tool in crystal engineering at the disposal of the supramolecular chemist.
Halogen bond
Lone pair
Crystal Engineering
Supramolecular assembly
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Six N-(4-halogenobenzyl)-3-halogenopyridinium cations were prepared by reacting meta-halogenopyridines (Cl, Br, and I) with (4-halogenobenzyl) bromides (Br and I) and were isolated as bromide salts, which were further used to obtain iodides and chlorides. Sixteen compounds (out of 18 possible cation/anion combinations) were obtained; two crystallized as hydrates and 14 as solvent free salts, 11 of which belonged to one isostructural series and 3 to another. All crystal structures comprise halogen-bonded chains, with the anion as an acceptor of two halogen bonds, with the pyridine and the benzyl halogen substituents of two neighboring cations. The halogen bonds with the pyridine halogen show a linear correlation between the relative halogen bond length and angle, which primarily depend on the donor halogen. The parameters of the other halogen bonds vary with all three halogens, indicating that the former halogen bond is the dominant interaction. This is also in accord with the calculated electrostatic potential in the σ-holes of the halogens and the thermal properties of the solids. The second isostructural group comprises combinations of the best halogen bond donors and acceptors, and features a more favorable halogen bond geometry of the dominant halogen bond, reaffirming its significance as the main factor in determining the structure.
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Acceptor
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5-Bromopyrazoles, rarely investigated by X-ray crystallography, showed interesting halogen bonding and inter-halogen contacts.
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Crystal (programming language)
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Halogen and hydrogen bonds [1] are most often associated with the structure of molecular crystals. Even weak specific interactions, such as halogen···halogen and CH···halogen contacts, can compete between themselves and with Kitaigorodski's close packing rule. The competition between halogen···halogen and CH···halogen interactions has been studied at high pressure for the series of six dihalomethanes CH 2 XY (X,Y = Cl, Br, I). They crystallize in several structural types of space groups Pbcn, C2/c, Pnma, Pna2 1 or Fmm2. In all these compounds and in their polymorphs the halogen···halogen and CH···halogen interactions persist despite considerable structural differences. The group of monohalomethanes (CH 3 X, X = Cl, Br, I) are the simplest organic polar compounds and ideal models for studying halogen···halogen and CH···halogen interactions. For these simplest haloalkanes, the halogen···halogen competition with CH···halogen bonds, scaled in the function of electrostatic potential in the Cl, Br, I series, is affected by pressure. Phase α-CH 3 Br, isostructural with CH 3 I (orthorhombic space group Pnma) and dominated by halogen···halogen bonds, is destabilized by pressure. At 1.5 GPa the ambient-pressure α-CH 3 Br phase transforms into phase β-CH 3 Br governed by CH···halogen interactions. Phase β of CH 3 Br is isostructural with CH 3 Cl, orthorhombic space group Cmc2 1 [2,3]. The CH 3 Br molecules are more evenly accommodated in space group Cmc2 1 and CH···halogen interactions are favoured by the close-packing effect.
Isostructural
Halogen bond
Orthorhombic crystal system
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The competition between hydrogen- and halogen-bonding interactions in complexes of 5-halogenated 1-methyluracil (XmU; X = F, Cl, Br, I, or At) with one or two water molecules in the binding region between C5-X and C4=O4 is investigated with M06-2X/6-31+G(d). In the singly-hydrated systems, the water molecule forms a hydrogen bond with C4=O4 for all halogens, whereas structures with a halogen bond between the water oxygen and C5-X exist only for X = Br, I, and At. Structures with two waters forming a bridge between C4=O and C5-X (through hydrogen- and halogen-bonding interactions) exist for all halogens except F. The absence of a halogen-bonded structure in singly-hydrated ClmU is therefore attributed to the competing hydrogen-bonding interaction with C4=O4. The halogen-bond angle in the doubly-hydrated structures (150-160°) is far from the expected linearity of halogen bonds, indicating that significantly non-linear halogen bonds may exist in complex environments with competing interactions.
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