Properties of Sulfur‐Sulfur Bonds

Steudel, Ralf

doi:10.1002/anie.197506551

Cited by 260 publications

(135 citation statements)

References 115 publications

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“…Although both values are close to S--S bond lengths (2.05 A) in organic disulfanes (RSSR, Oae, 1985;Steudel, 1975), the S1--$2 bond distance of 2.136 (1) A is longer than the S1--SI' bond length of 2.016(1)A. These bond distances are similar to those in thiosulfonates (Noordik & Vos, 1967;Wahl, Bordner, Harpp & Gleason, 1973) and in bis(dimethylsulfonyl) disulfide (S6rum, 1953).…”

supporting

confidence: 53%

“…These bond distances are similar to those in thiosulfonates (Noordik & Vos, 1967;Wahl, Bordner, Harpp & Gleason, 1973) and in bis(dimethylsulfonyl) disulfide (S6rum, 1953). Introduction of an O atom to sulfur causes a lengthening and weakening of the neighboring S--S bonds and a stengthening of the S---O bond (Steudel, 1975) (Mathieson & Robertson, 1949) and bis(dimethylsulfonyl) disulfide (Srrum, 1953), respectively. The S 1--$2--O 1, S 1--$2--O2 and $2--S 1--S 1' bond angles are 102.4 (1), 109.3 (1) and 103.8 (1) °, respectively, in (1).…”

mentioning

confidence: 99%

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Bis(tert-butylsulfonyl) Disulfide

Freeman¹,

Ma²,

Lin³

1995

Acta Crystallogr C

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supporting

confidence: 53%

mentioning

confidence: 99%

Bis(tert-butylsulfonyl) Disulfide

Freeman¹,

Ma²,

Lin³

1995

Acta Crystallogr C

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“…Several reviews on elemental sulfur and its properties are available. [126][127][128] The bond length of an S-S bond is 2.06 A°(± 0.02) and the bond angle θ = 74°(± 2). 129 Ab-initio calculations of torsional angles for polysulfanes (H 2 S n , n = 2...6) has been reported by Suleimenov and Tae-Kyu Ha.…”

Section: A Conformational Analysis Of Sulfur and Isoprene Chainsmentioning

confidence: 99%

Sulfur Vulcanization of Natural Rubber for Benzothiazole Accelerated Formulations: From Reaction Mechanisms to a Rational Kinetic Model

Ghosh

Katare

Patkar

et al. 2003

Rubber Chemistry and Technology

210

228

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The chemistry of accelerated sulfur vulcanization is reviewed and a fundamental kinetic model for the vulcanization process is developed. The vulcanization of natural rubber by the benzothiazolesulfenamide class of accelerators is studied, where 2-(morpholinothio) benzothiazole (MBS) has been chosen as the representative accelerator. The reaction mechanisms that have been proposed for the different steps in vulcanization chemistry are critically evaluated with the objective of developing a holistic description of the governing chemistry, where the mechanisms are consistent for all reaction steps in the vulcanization process. A fundamental kinetic model has been developed for accelerated sulfur vulcanization, using population balance methods that explicitly acknowledge the polysulfidic nature of the crosslinks and various reactive intermediates. The kinetic model can accurately describe the complete cure response including the scorch delay, curing and the reversion for a wide range of compositions, using a single set of rate constants. In addition, the concentration profiles of all the reaction intermediates as a function of polysulfidic lengths are predicted. This detailed information obtained from the population balance model is used to critically examine various mechanisms that have been proposed to describe accelerated sulfur vulcanization. The population balance model provides a quantitative framework for explicitly incorporating mechanistically reasonable chemistry of the vulcanization process.

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“…2.05 Å being reported. [18] The peri-angles in acenaphthylene are 120.3(8)°, 127.8(6)° and 120.3(8)° with the sum being 368.4°. [3] In L1 the sum of the bay angles is 348.32(28)° with a resulting negative splay angle of -11.7°; this is less than the sum in ideal acenaphthylene confirming a favourable interaction is occurring between the peri-atoms resulting in the formation of a peri-bond.…”

Section: Resultsmentioning

confidence: 99%

Acenaphtho[5,6-cd]-1,2-dichalcogenoles and their platinum complexes

et al. 2015

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A related series of bis(phosphine) platinum complexes 1-5 and 6-8 bearing dichalcogenate acenaphthylene ligands have been synthesised. The chalcogen-chalcogen bonds in the parent acenaphtho[5,6-cd]-1,2-dichalcogenoles (AcenapylE 2 ; L1 E = S, L2 E = Se; Acenapyl = acenaphthylene-5,6-diyl) were reduced with two equivalents of lithium triethylborohydride to form the dilithio-species. Metathetical addition of the lithium dichalcogenate species to a suspension of the appropriate cisdichlorobis(phosphine)platinum in THF resulted in the formation of platinum (II) complexes [Pt(5,6-AcenapylE 2 )(PR 3 ) 2 ] (1 E = S, R 3 = Ph 3 ; 2 E = S, R 3 = Ph 2 Me; 3 E = S, R 3 = PhMe 2 ; 4 E = S, R 3 = Me 3 ; 6 E = Se, R 3 = Ph 3 ; 7 E = Se, R 3 = Ph 2 Me; 8 E = Se, R 3 = PhMe 2 ). The dilithio-species of L1 and L2 were also reacted with (1,5-cyclooctadiene)platinum(II) dichloride.This reaction was successful with L1 resulting in the formation of platinum complex [Pt(5,6-AcenapylS 2 )(COD)] (5).Complexes 1-3 and 5-8 have been fully characterised, principally by multinuclear magnetic resonance spectroscopy, IR and MS. Secondary isotopomer effects create complex satellite systems observed in both the 31 P{ 1 H} NMR and 77 Se NMR spectra of selenium complexes 6-8. X-ray structures were determined for L1, 1, 3 and 6 and analysed, where appropriate, by measuring the peri-distance, splay angle magnitude, peri-atom displacement, central naphthalene ring torsions and the geometry around the platinum centre. Platinum was found to adopt a distorted square-planar geometry in all three complexes. Complex 1 was found to have the greatest molecular distortion of all three complexes, showing that changing the phosphine group and also the chalcogen has a noticeable effect. Comparisons were made between 6 and our previously reported [Pt(NapSe 2 )(PPh 3 ) 2 ] and [Pt(AcenapSe 2 )(PPh 3 ) 2 ] complexes; the level of distortion was found to decrease as the backbone is altered from naphthalene to acenaphthylene.

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Properties of Sulfur‐Sulfur Bonds

Cited by 260 publications

References 115 publications

Bis(tert-butylsulfonyl) Disulfide

Bis(tert-butylsulfonyl) Disulfide

Sulfur Vulcanization of Natural Rubber for Benzothiazole Accelerated Formulations: From Reaction Mechanisms to a Rational Kinetic Model

Acenaphtho[5,6-cd]-1,2-dichalcogenoles and their platinum complexes

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