Oxidation Methods for Aromatic Diazines: Substituted Pyrazine-N-Oxides, Pyrazine-N,n'-Dioxides, and 2,2':6',2"-Terpyridine-1,1"-Dioxide

McKay, Scott E.; Sooter, Joseph A.; Bodige, Satish G.; Blackstock, Silas C.

doi:10.1515/hc.2001.7.4.307

Cited by 11 publications

(3 citation statements)

References 10 publications

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“…Compound (I) was prepared using a modification of the procedure for direct oxidation of pyridine and pyrazine moieties (McKay et al, 2001). Dimethyldioxirane (17.71 ml, 0.08 M) in acetone was stirred with terpyridine (150.4 mg, 0.6447 mol, Aldrich 98%) in acetone (2 ml, Fisher reagent grade) for 5 d at 300 K. Filtration of the mixture provided terpyridine dioxide as a colorless solid [92.2%, 157.6 mg; m.p.…”

Section: Methodsmentioning

confidence: 99%

2,2′:6′,2′′-Terpyridine 1,1′′-dioxide dihydrate

2005

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The title compound, C15H11N3O3·2H2O, crystallizes with terpyridine dioxide molecules positioned on mirror planes in the space group Pnma. Catemeric assemblages of terpyridine molecules [C—H⋯−O—+N = 3.386 (4) Å] are linked by bridging water molecules [C—H⋯O = 3.288 (4) and 3.386 (4) Å; O—H⋯−O—+N = 2.837 (3) and 2.878 (4) Å], giving stacks of two‐dimensional undulating motifs.

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Section: Methodsmentioning

confidence: 99%

2,2′:6′,2′′-Terpyridine 1,1′′-dioxide dihydrate

2005

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“…2,2':6',2"-Terpyridine l,l"-dioxide was prepared using a modification of the procedure for direct oxidation of pyridine and pyrazine moieties [5]. Dimethyldioxirane (17.71 ml, 0.08 M) in acetone was stirred with terpyridine (150.4 mg, 0.6447 mol, Aldrich 98 %) in acetone (2 ml, Fisher reagent grade) for 5 d at 300 K. Filtration of the mixture provided terpyridine dioxide as a colorless solid (92.2 %, 157.6 mg; m.p.…”

Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of 2,2': 6', 2 " - terpyridinel 1,1" -dioxide 1,2,4,5 - tetracyanobenzene , C15H11N3O2 · C6H4(CN)4

Mckay¹,

Wheeler²,

Holthouse³

2006

Zeitschrift Für Kristallographie - New Crystal Structures

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“…2,2¢:6¢,2²-Terpyridine 1,1²-dioxide was prepared using a modification of the procedure for direct oxidation of pyridine and pyrazine moieties [5]. Dimethyldioxirane (17.71 ml, 0.08 M) in acetone was stirred with terpyridine (150.4 mg, 0.6447 mol, Aldrich 98 %) in acetone (2 ml, Fisher reagent grade) for 5 d at 300 K. Filtration of the mixture provided terpyridine dioxide as a colorless solid (92.2 %, 157.6 mg; m.p.…”

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confidence: 99%

Crystal structure of 2,2″:6′,2″-terpyridine 1,1″-dioxide 1,2,4,5-tetracyanobenzene, C15H11N3O2 · C6H4(CN)4

McKay

Wheeler

Holthouse

2006

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialWe have prepared the title compound as a continuing effort to understand the intermolecular contact preferences of the N-oxide group in molecular crystals [1][2][3][4]. 2,2¢:6¢,2²-Terpyridine 1,1²-dioxide was prepared using a modification of the procedure for direct oxidation of pyridine and pyrazine moieties [5]. Dimethyldioxirane (17.71 ml, 0.08 M) in acetone was stirred with terpyridine (150.4 mg, 0.6447 mol, Aldrich 98 %) in acetone (2 ml, Fisher reagent grade) for 5 d at 300 K. Filtration of the mixture provided terpyridine dioxide as a colorless solid (92.2 %, 157.6 mg; m.p. 502 507 K, cf. 505 506 K [6]). The title cocrystals were obtained by slow evaporation of a 1:1 mixture using the previously prepared 2,2¢:6¢,2²-terpyridine 1,1²-dioxide and commercially available 1,2,4,5-tetracyanobenzene in methylene chloride solution at room temperature. The oxidizing agent, dimethyldioxirane, was prepared by reacting potassium peroxomonosulfate (0.0390 mol) and NaHCO3 (0.138 mol) in acetone (38.4 ml) and water (50 ml) [7]. Vigorous stirring of the mixture at 263 K followed by distillation (40 100 Torr) at ambient temperature resulted in 0.06 0.08 M dimethyldioxirane as verified by titration against thioanisole. Experimental detailsThe aryl hydrogen atoms were located in a difference density map and refined isotropically. The CH distances were normalized to 1.08 Å for subsequent investigation of CH···O interactions. DiscussionThe crystal structure of this 1:1 bimolecular compound contains tetracyanobenzene (TCNB) and terpyridinedioxide (TPDO) molecules positioned on inversion and two-fold rotation symmetry elements, respectively. Inspection of molecular conformation reveals the expected planar TCNB with TPDO skewed due to the pyridyl-N-oxide-pyridyl geometry (ÐN10C9C8N1 = 145.7(1)°). The crystal structure is stabilized by an assortment of nonbonded contacts that link adjacent TCNB and TPDO building blocks. Each TCNB moiety forms C2AH···O15 N10

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Oxidation Methods for Aromatic Diazines: Substituted Pyrazine-N-Oxides, Pyrazine-N,n'-Dioxides, and 2,2':6',2"-Terpyridine-1,1"-Dioxide

Cited by 11 publications

References 10 publications

2,2′:6′,2′′-Terpyridine 1,1′′-dioxide dihydrate

2,2′:6′,2′′-Terpyridine 1,1′′-dioxide dihydrate

Crystal structure of 2,2': 6', 2 " - terpyridinel 1,1" -dioxide 1,2,4,5 - tetracyanobenzene , C15H11N3O2 · C6H4(CN)4

Crystal structure of 2,2″:6′,2″-terpyridine 1,1″-dioxide 1,2,4,5-tetracyanobenzene, C15H11N3O2 · C6H4(CN)4

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