A bis(1,2,3-dithiazole) charge transfer salt with 2 : 1 stoichiometry; inhibition of association and generation of slipped -stacks

Barclay, Tosha M.; Cordes, A. W.; Mingie, James R.; Oakley, Richard T.; Preuss, Kathryn E.

doi:10.1039/b004239k

Cited by 30 publications

(26 citation statements)

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“…Photometrical analysis with Nessler's reagent revealed NH 3 in 3 % yield. ; 19 F NMR: δ = 40.7 ppm; the structure was assigned tentatively). Crystallization (toluene) of the non-volatile residue from sublimation gave 13 (3 mg) as black crystals.…”

Section: Methodsmentioning

confidence: 99%

“…For the hydrocarbon analog of 12, a slipped π-stack structure with a head-to-head orientation of neighboring molecules is observed. [19] Eur. J. Inorg.…”

Section: Crystal and Molecular Structuresmentioning

confidence: 98%

“…In particular, the 6-6 bicyclic system of 1 and 2 transforms into differently fused 5-5-6, 5-6-7, and 5-6-6-6 polycyclic systems. (17) was detected in the reaction mixture by 19 F NMR spectroscopy and GLC-MS (Scheme 3; the structure was assigned tentatively by comparison with isomeric 12). In contrast to the thermolysis of 1, evolution of acidic gases was observed.…”

Section: Thermal Transformationsmentioning

confidence: 99%

“…610-635 nm. [1][2][3][4][5] The 5-5-6 (12 and its hydrocarbon analog [19] ), 5-6-7 (5, 13), and angular 5-6-6-6 (6, 14) systems reveal strong (log ε Ϸ 3.9-4.2) absorptions in about the same range of ca. 570-635 nm, whereas the linear 5-6-6-6 system 15 absorbs at shorter wavelengths (Table 1), with only a weak dependence of the corresponding πǞπ* transitions in extended polyheteroatom π-systems upon substitution of fluorine for hydrogen.…”

Section: Crystal and Molecular Structuresmentioning

confidence: 99%

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New Polysulfur‐Nitrogen Heterocycles by Thermolysis of 1,3λ⁴δ²,2,4‐Benzodithiadiazines in the Hydrocarbon and Fluorocarbon Series

et al. 2005

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In contrast to thermolysis of 1,3λ4δ2,2,4‐benzodithiadiazine (1) and its 5,6,7,8‐tetrafluoro derivative 2 in dilute (10–3 M) hydrocarbon solutions, which leads to persistent 1,2,3‐benzodithiazolyls in nearly quantitative yields, the thermolysis of 1 and 2 (the 6‐6 bicyclic system) in concentrated (0.5 M) solutions at 150–170 °C results in complex mixtures of various polysulfur‐nitrogen heterocycles, in particular differently fused 5‐5‐6, 5‐6‐7 and 5‐6‐6‐6 polycyclic systems that were previously unknown. The products were isolated by column chromatography, and the structures of the 5‐5‐6 (11, 12), 5‐6‐7 (5, 13), and 5‐6‐6‐6 (6, 14, 15) polycyclic systems, as well as the 6‐7 (4) and 5‐6 (16) bicyclic derivatives, confirmed by X‐ray diffraction. The crystal packing of 6 and 11–16 is discussed with special emphasis on π‐stacking interactions. The fluorescent properties of the 5‐6‐6‐6 systems synthesized are reported. An alternative approach to the linear 5‐6‐6‐6 system 15 based on self‐condensation of an R–N=PPh3 precursor (R = 4,5,6,7‐tetrafluoro‐1,2,3‐benzodithiazol‐2‐yl) is described, and the free‐radical character of this new reaction is proved. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Methodsmentioning

confidence: 99%

“…For the hydrocarbon analog of 12, a slipped π-stack structure with a head-to-head orientation of neighboring molecules is observed. [19] Eur. J. Inorg.…”

Section: Crystal and Molecular Structuresmentioning

confidence: 98%

Section: Thermal Transformationsmentioning

confidence: 99%

Section: Crystal and Molecular Structuresmentioning

confidence: 99%

See 2 more Smart Citations

New Polysulfur‐Nitrogen Heterocycles by Thermolysis of 1,3λ⁴δ²,2,4‐Benzodithiadiazines in the Hydrocarbon and Fluorocarbon Series

et al. 2005

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“…There are both face-to-face and edge-to-face π-π stacking [3 -4] interactions between aromatic rings belonging to two different ligands in this network. The thiazole groups of 2 are almost parallel and this parallel array of the planes of the aromatic moieties indicates that these interactions are of the face-to-face "π-stacking" type [4,5]. The centroid-centroid distance of thiazole groups is 3.92Å and the angle between the ring normal and the centroid vectors is 14.99.…”

Section: Resultsmentioning

confidence: 81%

Structure of the Cocrystal of 2,2’-Diamino-4,4’-bis(1,3-thiazole) and 4,4’-Bipyridine

Amiri

Ranjbar

Morsali

et al. 2006

Zeitschrift Für Naturforschung B

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A Novel One-Dimensional Coordination Polymer Involving Weak HgHg Interactions

Morsali

Kempe

2005

HCA

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The novel, stable, one-dimensional coordination polymer [Hg 3 (dmap) 6 (m-OAc) 2 ] n {(ClO 4 ) 4 } n (1; dmap 4-(dimethylamino)pyridine) has been synthesized and characterized. Single-crystal X-ray analysis showed that the coordination sphere of the two pertinent, zig-zag-oriented Hg II -atoms is different. One type of Hg-atom in the N 2 O 4 HgÀHgN 2 O 4 environment is seven-coordinate, with a weak HgÀHg interaction. The other type of Hg IIatom in the trans-HgN 2 O 4 units is six-coordinate.

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A bis(1,2,3-dithiazole) charge transfer salt with 2 : 1 stoichiometry; inhibition of association and generation of slipped -stacks

Cited by 30 publications

References 0 publications

New Polysulfur‐Nitrogen Heterocycles by Thermolysis of 1,3λ⁴δ²,2,4‐Benzodithiadiazines in the Hydrocarbon and Fluorocarbon Series

New Polysulfur‐Nitrogen Heterocycles by Thermolysis of 1,3λ⁴δ²,2,4‐Benzodithiadiazines in the Hydrocarbon and Fluorocarbon Series

Structure of the Cocrystal of 2,2’-Diamino-4,4’-bis(1,3-thiazole) and 4,4’-Bipyridine

A Novel One-Dimensional Coordination Polymer Involving Weak HgHg Interactions

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A bis(1,2,3-dithiazole) charge transfer salt with 2 : 1 stoichiometry; inhibition of association and generation of slipped -stacks

Cited by 30 publications

References 0 publications

New Polysulfur‐Nitrogen Heterocycles by Thermolysis of 1,3λ4δ2,2,4‐Benzodithiadiazines in the Hydrocarbon and Fluorocarbon Series

New Polysulfur‐Nitrogen Heterocycles by Thermolysis of 1,3λ4δ2,2,4‐Benzodithiadiazines in the Hydrocarbon and Fluorocarbon Series

Structure of the Cocrystal of 2,2’-Diamino-4,4’-bis(1,3-thiazole) and 4,4’-Bipyridine

A Novel One-Dimensional Coordination Polymer Involving Weak HgHg Interactions

Contact Info

Product

Resources

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New Polysulfur‐Nitrogen Heterocycles by Thermolysis of 1,3λ⁴δ²,2,4‐Benzodithiadiazines in the Hydrocarbon and Fluorocarbon Series

New Polysulfur‐Nitrogen Heterocycles by Thermolysis of 1,3λ⁴δ²,2,4‐Benzodithiadiazines in the Hydrocarbon and Fluorocarbon Series