Not Only Hydrogen Bonds: Other Noncovalent Interactions

Alkorta, Ibón; Elguero, José; Frontera, Antonio

doi:10.3390/cryst10030180

Cited by 301 publications

(258 citation statements)

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Section: Introductionmentioning

confidence: 99%

“…Short halogen···halogen contacts can be classified on two types ( Figure 1) [1]. Type I is simply due to crystal packing effects, while type II (halogen bonding) is directed noncovalent interactions [2] formed between the σ-hole (electrophilic region) on the halogen (Hal) atom and a nucleophile. Although both types of Hal···Hal contacts have similar abundance, today halogen bond (type II) has drawn significantly higher attention and similarly to hydrogen bonds, metallophilic contacts, Although both types of Hal···Hal contacts have similar abundance, today halogen bond (type II) has drawn significantly higher attention and similarly to hydrogen bonds, metallophilic contacts, and stacking interactions, halogen bonding is now widely used in crystal growth and design and in and stacking interactions, halogen bonding is now widely used in crystal growth and design and in supramolecular engineering [1,[3][4][5].…”

Section: Introductionmentioning

confidence: 99%

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Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide

et al. 2020

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4-Bromobenzamidrazone reacts with cyclopentanone giving 3-(4-bromophenyl)-5-(4-peroxobutyl)-1,2,4-triazole, which precipitated as pale-yellow crystals during the reaction. The intermolecular noncovalent interactions Br···Br in the single-crystal XRD structure of the peroxo compound were studied theoretically using quantum chemical calculations (ωB97XD/x2c-TZVPPall) and quantum theory of atoms in molecules (QTAIM) analysis. These attractive intermolecular noncovalent interactions Br···Br is type I halogen···halogen contacts and their estimated energy is 2.2–2.5 kcal/mol. These weak interactions are suggested to be one of the driving forces (albeit surely not the main one) for crystallization of the peroxo compound during the reaction and thus its stabilization in the solid state.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide

et al. 2020

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“…The most prominent example for the crucial role of non-covalent interactions is probably the double helix structure of DNA [ 2 , 3 ]. Different types of non-covalent interactions, such as hydrogen bonding, π⋯π interaction, halogen bonding, chalcogen bonding, pnictogen bonding, tetrel bonding, (an)agostic bonding, and cation/anion⋯π interaction, can be distinguished, and their role in all areas of molecular chemistry and biology is eminent [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ]. Amongst them, non-covalent π⋯π interactions, also called π-stacking, found between aromatic systems, are of great interest due to their broad applications [ 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 13 , 14 , 15 , 16 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Tetrel Bonding and Other Non-Covalent Interactions Assisted Supramolecular Aggregation in a New Pb(II) Complex of an Isonicotinohydrazide

et al. 2020

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A new supramolecular Pb(II) complex [PbL(NO2)]n was synthesized from Pb(NO3)2, N’-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide (HL) and NaNO2. [PbL(NO2)]n is constructed from discrete [PbL(NO2)] units with an almost ideal N2O3 square pyramidal coordination environment around Pb(II). The ligand L− is coordinated through the 2-pyridyl N-atom, one aza N-atom, and the carbonyl O-atom. The nitrite ligand binds in a κ2-O,O coordination mode through both O-atoms. The Pb(II) center exhibits a hemidirected coordination geometry with a pronounced coordination gap, which allows a close approach of two additional N-atoms arising from the N=C(O) N-atom of an adjacent molecule and from the 4-pyridyl N-atom from the another adjacent molecule, yielding a N4O3 coordination, constructed from two Pb–N and three Pb–O covalent bonds, and two Pb⋯N tetrel bonds. Dimeric units in the structure of [PbL(NO2)]n are formed by the Pb⋯N=C(O) tetrel bonds and intermolecular electrostatically enforced π+⋯π− stacking interactions between the 2- and 4-pyridyl rings and further stabilized by C–H⋯π intermolecular interactions, formed by one of the methyl H-atoms and the 4-pyridyl ring. These dimers are embedded in a 2D network representing a simplified uninodal 3-connected fes (Shubnikov plane net) topology defined by the point symbol (4∙82). The Hirshfeld surface analysis of [PbL(NO2)] revealed that the intermolecular H⋯X (X = H, C, N, O) contacts occupy an overwhelming majority of the molecular surface of the [PbL(NO2)] coordination unit. Furthermore, the structure is characterized by intermolecular C⋯C and C⋯N interactions, corresponding to the intermolecular π⋯π stacking interactions. Notably, intermolecular Pb⋯N and, most interestingly, Pb⋯H interactions are remarkable contributors to the molecular surface of [PbL(NO2)]. While the former contacts are due to the Pb⋯N tetrel bonds, the latter contacts are mainly due to the interaction with the methyl H-atoms in the π⋯π stacked [PbL(NO2)] molecules. Molecular electrostatic potential (MEP) surface calculations showed marked electrostatic contributions to both the Pb⋯N tetrel bonds and the dimer forming π+⋯π− stacking interactions. Quantum theory of atoms in molecules (QTAIM) analyses underlined the tetrel bonding character of the Pb⋯N interactions. The manifold non-covalent interactions found in this supramolecular assembly are the result of the proper combination of the polyfunctional multidentate pyridine-hydrazide ligand and the small nitrito auxiliary ligand.

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“…There is much interest nowadays in noncovalent interactions since they play a major role in many biological and chemical processes and also govern the behaviour of individual molecules in clusters of varying sizes and shapes. The hydrogen bond is the most well known and the most widely-studied noncovalent interaction [ 1 , 2 , 3 , 4 , 5 , 6 ], but interest has grown considerably in sigma-hole interactions over the last 15 years or so, with much attention initially given to halogen bonding [ 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

Interactions in Model Ionic Dyads and Triads Containing Tetrel Atoms

McDowell

Wang

2020

Molecules

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The interactions in model ionic YTX3···Z (Y = NC, F, Cl, Br; X = F, Cl, Br, Z = F−, Cl−, Br−, Li+) dyads containing the tetrel atoms, T = C, Si, Ge, were studied using ab initio computational methods, including an energy decomposition analysis, which found that the YTX3 molecules were stabilized by both anions (via tetrel bonding) and cations (via polarization). For the tetrel-bonded dyads, both the electrostatic and polarization forces make comparable contributions to the binding in the C-containing dyads, whereas, electrostatic forces are by far the largest contributor to the binding in the Si- and Ge-containing analogues. Model metastable Li+···NCTCl3···F− (T = C, Si, Ge) triads were found to be lower in energy than the combined energy of the Li+ + NCTCl3 + F− fragments. The pair energies and cooperative energies for these highly polar triads were also computed and discussed.

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Not Only Hydrogen Bonds: Other Noncovalent Interactions

Cited by 301 publications

References 263 publications

Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide

Symmetrical Noncovalent Interactions Br···Br Observed in Crystal Structure of Exotic Primary Peroxide

Tetrel Bonding and Other Non-Covalent Interactions Assisted Supramolecular Aggregation in a New Pb(II) Complex of an Isonicotinohydrazide

Interactions in Model Ionic Dyads and Triads Containing Tetrel Atoms

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