A survey of tellurium-centered secondary-bonding supramolecular synthons

Cozzolino, Anthony F.; Elder, Philip J. W.; Vargas‐Baca, Ignacio

doi:10.1016/j.ccr.2010.12.015

Cited by 174 publications

(110 citation statements)

References 92 publications

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“…The attractive nature of this interaction, arising from a combination of electrostatic, dispersion and charge transfer components, is supported by computational studies. 3,4 Self-association of chalcogen-based heterocycles (e.g., chalcogenadiazoles, chalcogenazoles) into chains, ribbons or cyclic aggregates is a notable manifestation of this effect. 2 Both interactions are most favourable for the heaviest elements in the group (Te 4 Se 4 S 4 O and I 4 Br 4 Cl 4 F), and display directionality, with the preferred geometry having a 1801 YÁ Á ÁE-R or YÁ Á ÁX-R angle (where Y is the Lewis base, E is a chalcogen, X is a halogen and R is a generic substituent).…”

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confidence: 99%

Anion recognition by a bidentate chalcogen bond donor

et al. 2016

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Anion recognition by a bidentate chalcogen bond donor

et al. 2016

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“…Iso-tellurazole N-oxides (1) have shown a remarkable ability to form aggregates through Te···O interactions. 21 4 , and [Te-1-O] 6 supramolecular synthons 23 -can be selectively obtained by modifying the crystallization conditions. NMR experiments have demonstrated that the cyclic oligomers are persistent in solution and exist in equilibrium.…”

Section: Introductionmentioning

confidence: 99%

Influence of acidic media on the supramolecular aggregation of iso-tellurazole N-oxides

Lee

Jenkins

et al. 2016

Can. J. Chem.

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Iso-tellurazole N-oxides are promising supramolecular building blocks. While in neutral solutions, they form tetraand hexameric macrocyclic aggregates linked by Te···O secondary bonding ( hole interactions or chalcogen bonds), protonation of the oxygen atom in acidic media disrupts such supramolecular association. The process is reversible and, consequently, can be used to switch on and off the self-assembly process. Hammett acidity measurements gave pK a values of -3.2 for the protonated molecules. Adducts with HCl and HBr were isolated and structurally characterized. Protonation in solution led to the crystallization of a new polymorph of 3-methyl-5-phenyl-1,2-tellurazole N-oxide, which features a unique polymeric arrangement. Résumé :Les isotellurazoles N-oxydes sont des synthons supramoléculaires prometteurs. Bien qu'en solution neutre, ils forment des agrégats macrocycliques tétramériques et hexamériques retenus par des liaisons secondaires Te···O (interactions de trous ou liaisons chalcogène), en milieu acide, la protonation des atomes d'oxygène perturbe une association supramoléculaire de ce type. Ce processus d'association est réversible et peut donc être utilisé pour provoquer ou inhiber le processus d'autoassamblage. Nous avons calculé, pour les molécules protonées, une valeur de pK a de -3,2 dérivée des mesures de l'acidité en utilisant l'équation de Hammett. En outre, nous avons isolé des adduits de HCl et de HBr et en avons caractérisé les structures. La protonation en solution a entraîné la cristallisation d'un nouveau polymorphe du 3-méthyl-5-phényl-1,2-tellurazole N-oxyde présentant une structure polymérique unique. [Traduit par la Rédaction]Mots-clés : interactions de trous sigma, liaison secondaire, chalcogènes, chimie supramoléculaire, chimie du groupement principal.

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“…A greater number of structures may help to establish this dependence. In this context, a study carried out on tellurium supramolecular synthons established that no correlation exists between secondary bond distance and the coordination number of tellurium (Cozzolino et al, 2011).…”

Section: The Te···x Contact In Organotellurium Compoundsmentioning

confidence: 99%

“…This chapter deals with the weak Te···halogen (Te···X) interactions found in organotellurium crystal structures and with the supramolecular arrangements derived from them. Some supramolecular self-assemblies based on Te···halogen secondary bonds have been described Zukerman-Schpector et al, 2002;Srivastava et al, 2004;Cozzolino et al, 2011). This chapter presents a systematic update including quantitative aspects.…”

Section: Introductionmentioning

confidence: 99%