Regioselective Synthesis of Bis(2-halo-3-pyridyl) Dichalcogenides (E = S, Se and Te): Directed Ortho-Lithiation of 2-halopyridines

Bhasin, K. K.; Singh, Neelam; Doomra, Shivani; Arora, Ekta; Ram, Ganga; Singh, Sukhwinder; Nagpal, Yogesh; Mehta, S.K.; Klapötke, Thomas M.

doi:10.1155/2007/69263

Cited by 19 publications

(7 citation statements)

References 19 publications

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“…27 Chemical structures for the three ''hits'', i.e. 1-3, [34][35][36] are shown in Scheme 2 and geometric parameters describing the contacts are given in Table 1. Each of 1-3 self-associates to form supramolecular chains with helical, zig-zag and linear topologies, respectively, Fig.…”

Section: Preamblementioning

confidence: 99%

A structural survey of metal⋯π heteroaromatic supramolecular synthons for metal = tellurium, tin, and gold

Tiekink

Zukerman-Schpector

2009

CrystEngComm

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A survey of tellurium, tin and gold structures containing metal/p heteroaromatic interactions has been conducted, and their occurrence correlated with previously described metal/p aryl interactions. Metal/p heteroaromatic interactions are found for all three metals when the heteroaromatic ring was a pyridine/pyridine-derivative, and these contacts lead usually to 0-D or 1-D aggregates with rare examples of 2-D and 3-D architectures. For each of tellurium and tin, metal/p aryl interactions are more likely to form over metal/p pyridine interactions, while the reverse is true in the case of gold. These observations are readily correlated with the influence of increasing electron density in the pyridine compared with an aryl ring. In the case of tellurium and tin, for which the metal/p interaction involves a metal-based lone pair of electrons being donated to the LUMO of the aryl group, increasing the electron density of the aromatic ring naturally decreases the probability of forming this type of interaction. In the case of gold, where the metal/p interaction involves the donation of electron density from the aromatic ring to the gold centre, increasing the electron density of the aromatic ring favours such an interaction. At least for the metals surveyed, metal/p interactions are observed in a significant number of their crystal structures, for example up to 6% of all tellurium structures feature Te/p aryl interactions as a supramolecular synthon.

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Section: Preamblementioning

confidence: 99%

A structural survey of metal⋯π heteroaromatic supramolecular synthons for metal = tellurium, tin, and gold

Tiekink

Zukerman-Schpector

2009

CrystEngComm

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“…The three remaining crystals of tellurium congeners presented different supramolecular association patterns. In 5Te , 77 Te⋯N separations longer than the sum of the van der Waals radii occur within a twisted ribbon as opposed to the dimeric aggregates formed by the three independent molecules of 5 , Fig. 2(e).…”

Section: An Evaluation Of Congeners Of 1–88 For the Presence Of Relat...mentioning

confidence: 98%

“…The next two molecules feature Se–Se bonds. In 5 , 77 three independent molecules comprise the crystallographic asymmetric-unit. One of these self-associated about a centre of inversion to form a dimer featuring a 10-membered {⋯Se 2 C 2 N} 2 synthon; this corresponds to the shorter Se⋯N separation for this entry in Table 1.…”

Section: Supramolecular Architectures Featuring Di-nuclear Selenium M...mentioning

confidence: 99%

Supramolecular architectures featuring Se⋯N secondary-bonding interactions in crystals of selenium-rich molecules: a comparison with their congeners

Tiekink

2023

CrystEngComm

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“…In the present study, efforts have been made to solubilize the water-insoluble organic derivative of chalcogen, that is, bis(diphenylmethyl)diselenide [(C 6 H 5 ) 2 CHSe] 2 and 3,3′-dibromo-4,4′-dimethyl-2-dipyridyl diselenide [C 12 H 10 N 2 Se 2 Br 2 ] in single, binary, and ternary surfactant mixtures of hexadecyl (C 16 ) chain length surfactant having cationic and nonionic head groups. These chalcogenides are rigid nonplanar moieties having bulky selenium bridge and find potential applications in synthesis of various Se compounds. − The evaluation of solubilization capabilities of equimolar cationic−nonionic, cationic−cationic, and cationic−cationic−nonionic mixed systems have also been investigated. The systems were investigated using static fluorescence and UV−visible spectroscopy, surface tension, and conductivity.…”

Section: Introductionmentioning

confidence: 99%

“…These chalcogenides are rigid nonplanar moieties having bulky selenium bridge and find potential applications in synthesis of various Se compounds. [33][34][35] The evaluation of solubilization capabilities of equimolar cationic-nonionic, cationic-cationic, and cationic-cationic-nonionic mixed systems have also been investigated. The systems were investigated using static fluorescence and UV-visible spectroscopy, surface tension, and conductivity.…”

Section: Introductionmentioning

confidence: 99%

Facile Solubilization of Organochalcogen Compounds in Mixed Micelle Formation of Binary and Ternary Cationic−Nonionic Surfactant Mixtures

et al. 2009

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This study investigated the water solubility enhancements of organochalcogen compounds, viz. bis(diphenylmethyl)diselenide [(C6H5)2CHSe]2 and 3,3'-dibromo-4,4'-dimethyl-2-dipyridyl diselenide [C12H10N2Se2Br2] in micellar media. Two cationic and one nonionic surfactants possessing the same hydrocarbon tail, namely hexadecyltrimethylammonium bromide (C16Br), hexadecyltrimethylammonium chloride (C16Cl), and polyoxyethylene(20)mono-n-hexadecyl ether (Brij 58), in their single as well as equimolar binary and ternary mixed states have been used. Solubilization capacity has been evaluated in terms of the molar solubilization ratio and the micelle water partition coefficients. The association constants between the solubilizate molecules and that of micelle and the average number of solubilizate molecules per micelle have also been quantified. The results showed that cationic surfactants exhibit less solubilization as compared to nonionic surfactant. The mixing effects of surfactants on micelle formation and solubilization efficiencies have also been discussed. It has been observed that cationic-nonionic binary combinations showed better solubilization capacity as compared to pure cationic, nonionic, or cationic-cationic binary mixtures. An equimolar cationic-cationic-nonionic ternary surfactant system provides higher solubilization than cationic-cationic but lowers than their cationic-nonionic counterpart. In addition, Fourier transform infrared has been employed with fair success to predict the information regarding the aggregates and the mechanism of docking of the surfactant and the chalcogenides in the system. The analysis has provided valuable information for the selection of mixed surfactants for solubilizing water-insoluble compounds. Certainly the solubilization ability of these surfactants is not simply related to molar capacity. The results give sufficient encouragement to warrant more detailed investigation of the features of surfactant properties that affect solubilization.

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Regioselective Synthesis of Bis(2-halo-3-pyridyl) Dichalcogenides (E = S, Se and Te): Directed Ortho-Lithiation of 2-halopyridines

Cited by 19 publications

References 19 publications

A structural survey of metal⋯π heteroaromatic supramolecular synthons for metal = tellurium, tin, and gold

A structural survey of metal⋯π heteroaromatic supramolecular synthons for metal = tellurium, tin, and gold

Supramolecular architectures featuring Se⋯N secondary-bonding interactions in crystals of selenium-rich molecules: a comparison with their congeners

Facile Solubilization of Organochalcogen Compounds in Mixed Micelle Formation of Binary and Ternary Cationic−Nonionic Surfactant Mixtures

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