Naphthalene 1,8-Disulfide

Zweig, Arnold; Hoffmann, Arthur Kentaro

doi:10.1021/jo01023a001

Cited by 87 publications

(45 citation statements)

References 2 publications

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“…The intrinsic dipole moment of a C 6 H 5 S fragment was estimated some time ago to be 1.31 D [18]. If we use our measured value with their estimate of the dipole moment of two such fragments, one calculates the value of the angle between the two C-S vectors as 77Њ, whereas our observed value is approximately 60Њ.…”

Section: The Electric Dipole Moment Of I and Its Effect On Packingmentioning

confidence: 88%

“…Compound I was prepared by a procedure closely related to that of Zweig and Hoffman [18] and described in Ricci's thesis (see Ref.…”

Section: Experimental Synthesesmentioning

confidence: 99%

“…The details of data collection are summarized in Tables 1 and 2, respectively, for compounds I and II. The intensity data for II were corrected for absorption using empirical curves derived from Psi scans [17,18] of suitable reflections.…”

Section: Crystallographymentioning

confidence: 99%

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The phenomenon of conglomerate crystallization of organic compounds. Part 4. The structures of 2,2?-biphenyldisulfide (I) and 2,2?-biphenyldisulfide monoxide (II)

1998

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A racemic solution of 2,2′‐biphenyldisulfide (I), C12H8S2, produces conglomerate crystals of (I) belonging in space group P3221 (no. 154) with lattice constants: a = 7.38 (3) Å, b = 7.38 (3), c = 16.20 (2) Å; V = 766.6 Å3 and d(calc; M.W. = 216.32, z = 3) = 1.406 g‐cm−3, d(meas) = 1.47 g‐cm−3. A total of 1150 data were collected over the range of 4° ≤ 2θ ≤ 60° using film data (Weissenberg); of these, 448 [independent and with I ≥ 3σ(I)] were used in the structural analysis. Refinement converged to final residuals of 0.080 and 0.082 for R(F) and RW(F), respectively. The molecule is located at the twofold axis of the space group. A solution of 2,2′‐biphenyldisulfide mono‐oxide (II), C12H8S2O, produces centrosymmetric crystals of II belonging in space group P21/c with lattice constants: a = 9.947 (1) Å, b = 7.162 (2), c = 15.420 (3) Å, and β = 107.56 (1)°; V = 107.56 (1) Å3 and d(calc; M.W. = 232.31, Z = 4) = 1.473 g‐cm−3. A total of 2114 data were collected over the range of 4° ≤ 2θ ≤ 50°; of these, 1089 [independent and with I ≥ 2.5σ(I)] were used in the structural analysis. Data were corrected for absorption (μ = 4.539 cm−1), and the relative transmission coefficients ranged from 0.9198 to 0.9998. Refinement converged to final residuals of 0.0313 and 0.0300 for R(F) and Rw(F), respectively. For I, the central six‐membered ring C4S2 contains a helical C2S2 fragment whose conformational chirality is defined by a torsional angle of 59.98°. The benzene rings are the expected, planar hexagons characteristic of aryl rings. By comparison with I, the torsional angle of the C2S2 fragment of the mono‐oxide is diminished (52.9°) by the introduction of the S=O fragment. We believe alteration of molecules (such as functionalization) causing large changes in torsional angles of helical fragments of molecules may play a role in the selection of their crystallization mode; however, it is not the only factor dictating that choice, which is also affected by steric hindrance to the formation of short intermolecular contacts leading, in the solid state, to the formation of homochiral, infinite helical strings, as we shall demonstrate in the text. This study clearly shows the influence of those contacts on the formation of the strings. © 1998 John Wiley & Sons, Inc. Heteroatom Chem 9:65–74, 1998

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Section: The Electric Dipole Moment Of I and Its Effect On Packingmentioning

confidence: 88%

“…Compound I was prepared by a procedure closely related to that of Zweig and Hoffman [18] and described in Ricci's thesis (see Ref.…”

Section: Experimental Synthesesmentioning

confidence: 99%

See 1 more Smart Citation

The phenomenon of conglomerate crystallization of organic compounds. Part 4. The structures of 2,2?-biphenyldisulfide (I) and 2,2?-biphenyldisulfide monoxide (II)

1998

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“…6, 8 Oxidation of 3 to the sulfinyl sulfone 4 has been previously carried out using basic hydrogen peroxide, 9 and we found that urea-hydrogen peroxide (UHP) is equally effective in this respect, providing 4 in more reproducible yields. Treatment of 4 under nitrosylating conditions gave formal nitrogen insertion into the sulfur-sulfur bond.…”

Section: Synthesis and Analysis Of 18-bissulfonylhydroxylaminementioning

confidence: 90%

In search of a new class of stable nitroxide: synthesis and reactivity of a peri-substituted N,N-bissulfonylhydroxylamine

et al. 2011

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Acyclic bissulfonylnitroxides have never been isolated, and degrade through fragmentation. In an approach to stabilising a bissulfonylnitroxide radical, the cyclic, peri-substituted N, N-bissulfonylhydroxylamine, 2-hydroxynaphtho[1,8-de][1,3,2]dithiazine 1,1,3,3-tetraoxide (1), has been prepared by formal nitrogen insertion into the sulfur-sulfur bond of a sulfinylsulfone, naphtho[1,8-cd][1,2]dithiole 1,1,2-trioxide. The heterocyclic ring of 1 is shown to adopt a sofa conformation by X-ray crystallography, with a pseudo-axial hydroxyl group. N,N-Bissulfonylhydroxylamine 1 displays high thermal, photochemical and hydrolytic stability compared to acyclic systems. EPR analysis reveals formation of the corresponding bissulfonylnitroxide 2 upon oxidation of 1 with the Ce(IV) salts CAN and CTAN. Although 2 does not undergo fragmentation, it cannot be isolated, since hydrogen atom abstraction to reform 1 occurs in situ. The stability and reactivity of 1 and 2 are compared with the known cyclic benzo-fused N,N-bissulfonylhydroxylamine, N-hydroxy-O-benzenedisulfonimide (6), for which the X-ray data, and EPR of the corresponding nitroxide 10, are also reported for the first time.

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“…Elemental analyses were carried out by Chemical Analysis Center at this University. Naphtho[1,8-cd]-1,2-dithiole (4) was prepared according to the method reported in the literature [13]. 1,8-Naphthalenedithiole (5) was prepared by the reduction of 4 with NaBH 4 in ethanol-THF [14].…”

Section: Methodsmentioning

confidence: 99%

New consecutive photochemical reactions of naphtho[1,8-de]-1,3-dithiin-1-N-tosylsulfilimines via the through-space interaction between two sulfur atoms; A convenient method for preparation ofN-tosylaldimines

1998

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Naphtho[1,8‐de]‐1,3‐dithiin‐1‐N‐tosylsulfilimines underwent facile consecutive photochemical reactions to give quantitatively the corresponding N‐tosylaldimines, together with naphtho[1,8‐cd]‐1,2‐dithiole, via a sulfur–sulfur interaction. The intermediate, 3‐hydro‐3‐phenyl‐naphtho[1,8‐ef][1,4]dithia[2]‐azepin, was isolated by liquid chromatography of the reaction mixtures, and its structure was determined by X‐ray crystallographic analysis. The proposed mechanism for these photochemical reactions is based on quantum yield measurements, photo‐intensity effects, and crossover experiments. © 1998 John Wiley & Sons, Inc. Heteroatom Chem 9:29–40, 1998

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Naphthalene 1,8-Disulfide

Cited by 87 publications

References 2 publications

The phenomenon of conglomerate crystallization of organic compounds. Part 4. The structures of 2,2?-biphenyldisulfide (I) and 2,2?-biphenyldisulfide monoxide (II)

The phenomenon of conglomerate crystallization of organic compounds. Part 4. The structures of 2,2?-biphenyldisulfide (I) and 2,2?-biphenyldisulfide monoxide (II)

In search of a new class of stable nitroxide: synthesis and reactivity of a peri-substituted N,N-bissulfonylhydroxylamine

New consecutive photochemical reactions of naphtho[1,8-de]-1,3-dithiin-1-N-tosylsulfilimines via the through-space interaction between two sulfur atoms; A convenient method for preparation ofN-tosylaldimines

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