Anion recognition based on halogen, chalcogen, pnictogen and tetrel bonding

Taylor, Mark S.

doi:10.1016/j.ccr.2020.213270

Cited by 180 publications

(183 citation statements)

References 166 publications

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“…We can mention first the association on the same molecule of strong ChB donor and acceptor sites, as in 1,2,5-telluradiazoles, [18] 1,2-chalcogenazole N-oxide, [19,20] benzo-1,3-chalcogenazole, [21] favoring the formation of infinite ribbons [18,22] or discrete supramolecular assemblies. [23] The use of ChB donors in organocatalysis [24,25] or anion recognition [26,27] processes involves the preparation of bidentate chelating molecules bearing two activated chalcogen atoms, able to interact with one single Lewis base, neutral or anionic, as found in molecules linking two tellurophenes, [28] two 5-(methylchalcogeno)-1,2,3-triazole moieties, [29] two thiophene units bearing Electron Withdrawing Groups (EWG), [30] or two selenocyanate groups. [31] In several examples, one of the two substituents linked to the chalcogen atom has a strong EWG character, favoring the formation of a stronger s-hole in the prolongation of this EWG-Ch bond.…”

Section: Introductionmentioning

confidence: 99%

Activating Chalcogen Bonding (ChB) in Alkylseleno/Alkyltelluroacetylenes toward Chalcogen Bonding Directionality Control

et al. 2020

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Activation of a deep electron‐deficient area on chalcogen atoms (Ch=Se, Te) is demonstrated in alkynyl chalcogen derivatives, in the prolongation of the (C≡)C−Ch bond. The solid‐state structures of 1,4‐bis(methylselenoethynyl)perfluorobenzene (1Se) show the formation of recurrent chalcogen‐bonded (ChB) motifs. Association of 1Se and the tellurium analogue 1Te with 4,4′‐bipyridine and with the stronger Lewis base 1,4‐di(4‐pyridyl)piperazine gives 1:1 co‐crystals with 1D extended structures linked by short and directional ChB interactions, comparable to those observed with the corresponding halogen bond (XB) donor, 1,4‐bis(iodoethynyl)‐perfluorobenzene. This “alkynyl” approach for chalcogen activation provides the crystal‐engineering community with efficient, and neutral ChB donors for the elaboration of supramolecular 1D (and potentially 2D or 3D) architectures, with a degree of strength and predictability comparable to that of halogen bonding in iodoacetylene derivatives.

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Section: Introductionmentioning

confidence: 99%

Activating Chalcogen Bonding (ChB) in Alkylseleno/Alkyltelluroacetylenes toward Chalcogen Bonding Directionality Control

et al. 2020

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“…These interactions can be divided into σ–hole [ 21 , 22 , 23 , 24 ] and π–hole interactions [ 25 , 26 , 27 , 28 , 29 ] and are nowadays entered into the toolkit supramolecular chemists. Actually, tetrel (Tt) [ 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ], pnictogen (Pn) [ 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 ], and chalcogen (Ch) [ 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 ] bonding interactions (see Figure 1 ) have been studied by many theoretical works and are progressively used experimentally in relevant fields such as supramolecular catalysis, polymers, transmembrane ion transport and, especially, crystal engineering [ 15 , …”

Section: Introductionmentioning

confidence: 99%

Noble Gas Bonding Interactions Involving Xenon Oxides and Fluorides

Frontera

2020

Molecules

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Noble gas (or aerogen) bond (NgB) can be outlined as the attractive interaction between an electron-rich atom or group of atoms and any element of Group-18 acting as an electron acceptor. The IUPAC already recommended systematic nomenclature for the interactions of groups 17 and 16 (halogen and chalcogen bonds, respectively). Investigations dealing with noncovalent interactions involving main group elements (acting as Lewis acids) have rapidly grown in recent years. They are becoming acting players in essential fields such as crystal engineering, supramolecular chemistry, and catalysis. For obvious reasons, the works devoted to the study of noncovalent Ng-bonding interactions are significantly less abundant than halogen, chalcogen, pnictogen, and tetrel bonding. Nevertheless, in this short review, relevant theoretical and experimental investigations on noncovalent interactions involving Xenon are emphasized. Several theoretical works have described the physical nature of NgB and their interplay with other noncovalent interactions, which are discussed herein. Moreover, exploring the Cambridge Structural Database (CSD) and Inorganic Crystal Structure Database (ICSD), it is demonstrated that NgB interactions are crucial in governing the X-ray packing of xenon derivatives. Concretely, special attention is given to xenon fluorides and xenon oxides, since they exhibit a strong tendency to establish NgBs.

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“…Chalcogen bonds (ChBs) result from interaction between an electrophilic region of a Group VI element (i.e., S, Se, Te) and a Lewis base. Due to their strength and directionality (comparable to hydrogen and halogen bonds) ChBs are intriguing alternatives to the predominant hydrogen bonding in various areas of research including crystal engineering, organic reactivity and catalysis [16,17], as well as anion transport and recognition [13,18,19].…”

Section: Introductionmentioning

confidence: 99%

Effect of Aromatic System Expansion on Crystal Structures of 1,2,5-Thia- and 1,2,5-Selenadiazoles and Their Quaternary Salts: Synthesis, Structure, and Spectroscopic Properties

et al. 2020

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Rational manipulation of secondary bonding interactions is a crucial factor in the construction of new chalcogenadiazole-based materials. This article reports detailed experimental studies on phenanthro[9,10-c][1,2,5]chalcogenadiazolium and 2,1,3-benzochalcogenadiazolium salts and their precursors. The compounds were synthesized, characterized employing NMR and UV-Vis spectroscopy. TD-DFT calculations were also performed. The influence of the size of the aromatic system on the molecular motifs formed by the compounds in the solid state has been studied by means of single-crystal X-ray diffraction. In case of the salts, the nature of an anion was also taken into consideration. The results show that cyclic [E···N]2 supramolecular synthon connects neighboring molecules of phenanthro[9,10-c][1,2,5]chalcogenadiazoles, with a relatively large aromatic system, in dimers regardless of the chalcogen atom in the molecule. Both N-methyl-2,1,3-benzothiadiazolium and N-methylphenanthro[9,10-c][1,2,5]chalcogenadiazolium cations have a strong affinity for triflate and iodide anions, therefore the formation of S···N or Se···N secondary bonding interactions is observed only in two out of the eight quaternary salts. Less coordinating anions must be used to enable the building blocks studied to form cyclic [E···N]2 synthons. Moreover, for two of the triflate salts, which are isostructural, a new supramolecular motif has been observed.

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Anion recognition based on halogen, chalcogen, pnictogen and tetrel bonding

Cited by 180 publications

References 166 publications

Activating Chalcogen Bonding (ChB) in Alkylseleno/Alkyltelluroacetylenes toward Chalcogen Bonding Directionality Control

Activating Chalcogen Bonding (ChB) in Alkylseleno/Alkyltelluroacetylenes toward Chalcogen Bonding Directionality Control

Noble Gas Bonding Interactions Involving Xenon Oxides and Fluorides

Effect of Aromatic System Expansion on Crystal Structures of 1,2,5-Thia- and 1,2,5-Selenadiazoles and Their Quaternary Salts: Synthesis, Structure, and Spectroscopic Properties

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