Chalcogen bonding in materials chemistry

Ho, Peter C.; Wang, Jin Z.; Meloni, Francesca; Vargas‐Baca, Ignacio

doi:10.1016/j.ccr.2020.213464

Cited by 98 publications

(98 citation statements)

References 82 publications

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“…The full range of these sorts of bonds, along with their designations, is summarized in Figure 1. processes [53][54][55][56][57][58][59][60][61], materials chemistry [62][63][64][65][66][67][68][69][70][71][72], or biochemistry [73][74][75][76][77][78][79][80][81]. An early work connecting σ-hole bonds with crucial concepts in chemistry occurred when Grabowski recognized that tetrel bonds can be thought of as a preliminary stage of the very important SN2 reaction [82].…”

Section: Introductionmentioning

confidence: 99%

“…As examples, understanding the forces behind crystal engineering and supramolecular chemistry benefits from a knowledge of σ-hole interactions due to their directionality, strength, and self-organization properties which promote formation of adducts in the solid state [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ]. The importance of σ-hole bonding has also been verified in the context of anion recognition processes [ 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 ], materials chemistry [ 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 ], or biochemistry [ 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 ]. An early work connecting σ-hole bonds with crucial concepts in chemistry occurred when Grabowski recognized that tetrel bonds can be thought of as a preliminary stage of the very important S N 2 reaction ...…”

Section: Introductionmentioning

confidence: 99%

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Noncovalent Bonds through Sigma and Pi-Hole Located on the Same Molecule. Guiding Principles and Comparisons

2021

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Over the last years, scientific interest in noncovalent interactions based on the presence of electron-depleted regions called σ-holes or π-holes has markedly accelerated. Their high directionality and strength, comparable to hydrogen bonds, has been documented in many fields of modern chemistry. The current review gathers and digests recent results concerning these bonds, with a focus on those systems where both σ and π-holes are present on the same molecule. The underlying principles guiding the bonding in both sorts of interactions are discussed, and the trends that emerge from recent work offer a guide as to how one might design systems that allow multiple noncovalent bonds to occur simultaneously, or that prefer one bond type over another.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Noncovalent Bonds through Sigma and Pi-Hole Located on the Same Molecule. Guiding Principles and Comparisons

2021

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“…Chalcogen bonding (ChB), [1–7] i. e. the attractive supramolecular interaction of electrophilic sites on atoms of heavy group 16‐elements (S, Se, Te) with electron‐rich centers, has unveiled an array of fascinating chemistry in fields as diverse as Lewis‐acid catalysis, [8–15] optical probes, [14,16,17] functional materials, [5,18–24] crystal engineering, [25–30] ion recognition and transport, [22,31–36] and protein folding [37] …”

Section: Methodsmentioning

confidence: 99%

Competing Effects of Chlorination on the Strength of Te⋅⋅⋅O Chalcogen Bonds Select the Structure of Mixed Supramolecular Macrocyclic Aggregates of Iso‐Tellurazole N‐Oxides

Lomax

Tomassetti

et al. 2021

Chemistry A European J

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Chlorination of 3-methyl-5-phenyl-1,2-tellurazole-2-oxide yielded the λ 4 Te dichloro derivative. Its crystal structure demonstrates that the heterocycle retains its ability to autoassociate by chalcogen bonding (ChB) forming macrocyclic tetramers. The corresponding Te•••O ChB distances are 2.062 Å, the shortest observed to date in aggregates of this type. DFTÀ D3 calculations indicate that while the halogenated molecule is stronger as a ChB donor it also is a weaker ChB acceptor; the overall effect is that the ChBs in the chlorinated homotetramer are not significantly stronger. However, partial halogenation or scrambling selectively yield the 2 : 2 heterotetramer with alternating λ 4 Te and λ 2 Te centers, which calculations identified as the thermodynamically preferred arrangement.Chalcogen bonding (ChB), [1][2][3][4][5][6][7] i. e. the attractive supramolecular interaction of electrophilic sites on atoms of heavy group 16elements (S, Se, Te) with electron-rich centers, has unveiled an array of fascinating chemistry in fields as diverse as Lewis-acid catalysis, [8][9][10][11][12][13][14][15] optical probes, [14,16,17] functional materials, [5,[18][19][20][21][22][23][24] crystal engineering, [25][26][27][28][29][30] ion recognition and transport, [22,[31][32][33][34][35][36] and protein folding. [37] Amongst the many molecules capable of forming ChBs, isotellurazole N-oxides (1, Scheme 1) stand apart because of their ability to spontaneously assemble cyclic tetramers (1 4 ) and hexamers (1 6 ) that exist in equilibrium in solution. [38][39][40] There are two electrophilic regions on the tellurium atom of 1, antipodal to each the NÀ Te and the CÀ Te bonds. The former has a larger V max and, consequently, the Te•••O ChB interaction in all known cases is formed trans to the N atom (e. g. 1 4,6 in Scheme 1). The Te•••O ChBs are reversible, scrambling is[a] P.

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“…The description and discussion of Se … N interactions in the crystals of mono-nuclear selenium compounds and their relationship with congeners points to an exciting future for investigations in this area, especially when the dimensionality of the supramolecular aggregates can be readily increased by increasing the number of selenium (or tellurium) atoms, having mixed species, etc. While opportunities exist for interesting crystal engineering exercises [30,33,205,206], the importance of chalcogen-bonding in biological applications and materials chemistry provide future impetus for work in this area [32,[207][208][209]].…”

Section: Overviewmentioning

confidence: 99%

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Tiekink

2021

Coordination Chemistry Reviews

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An evaluation of the Cambridge Structural Database for crystals containing Se … N secondary--bonding interactions was conducted. The presence of Se … N secondary-bonding interactions has been established in nearly 9% of crystals of mono-nuclear selenium compounds where such interactions can potentially form, that is, having at least one nitrogen atom. The Se … N interactions feature in 71 zero-dimensional, usually di-nuclear aggregates, 63 one-dimensional chains and tapes, and smaller numbers of two-and three-dimensional arrays, that is seven and one, respectively. Selenium(II) compounds form the majority of the dataset with only eight selenium(IV) compounds included in the survey. In most cases (112 out of 142), the selenium centre forms a single Se … N contact with 26 aggregates having a selenium atom forming two contacts and four examples where three Se … N contacts are evident. The great propensity of selenadiazole rings (75%) and selenocyanates (50%) to form Se … N secondary-bonding interactions in their crystals is particularly noteworthy.

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Chalcogen bonding in materials chemistry

Cited by 98 publications

References 82 publications

Noncovalent Bonds through Sigma and Pi-Hole Located on the Same Molecule. Guiding Principles and Comparisons

Noncovalent Bonds through Sigma and Pi-Hole Located on the Same Molecule. Guiding Principles and Comparisons

Competing Effects of Chlorination on the Strength of Te⋅⋅⋅O Chalcogen Bonds Select the Structure of Mixed Supramolecular Macrocyclic Aggregates of Iso‐Tellurazole N‐Oxides

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

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