Disulfur dichloride 4762467 215567452 2008-05-28T19:46:38Z DOI bot 6652755 Citation maintenance. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{Chembox new | Name = Disulfur dichloride | ImageFile = Disulfur-dichloride-2D-dimensions.png <!-- | ImageSize = 220px --> | ImageName = Structure and dimensions of the disulfur dichloride molecule | ImageFile1 = Disulfur-dichloride-3D-balls.png <!-- | ImageSize1 = 140px --> | ImageName1 = Ball-and-stick model of disulfur dichloride | ImageFile2 = Disulfur-dichloride-3D-vdW.png <!-- | ImageSize2 = 140px --> | ImageName2 = Space-filling model of disulfur dichloride | IUPACName = Sulfur(I) chloride | OtherNames = Disulfur dichloride<br /> Sulfur monochloride | Section1 = {{Chembox Identifiers | SMILES = ClSSCl | CASNo = 10025-67-9 | RTECS = WS4300000 }} | Section2 = {{Chembox Properties | Formula = S<sub>2</sub>Cl<sub>2</sub> | MolarMass = 135.04 g/mol | Appearance = yellow liquid | Density = 1.688 g/cm³, liquid | Solubility = decomp with loss of HCl | MeltingPt = –80 °C | BoilingPt = 137.1 °C | RefractIndex = 1.658 }} | Section3 = {{Chembox Structure | Coordination = gauche | Dipole = }} | Section7 = {{Chembox Hazards | ExternalMSDS = | MainHazards = corrosive | NFPA-H = 2 | NFPA-R = 1 | NFPA-F = 1 | RPhrases = 14-20-25-29-35-50 | SPhrases = 26-36/37/39-45-61 }} | Section8 = {{Chembox Related | OtherCpds = [[Sulfur dichloride|SCl<sub>2</sub>]]<br />[[Sulfuryl chloride|SO<sub>2</sub>Cl<sub>2</sub>]]<br />[[Sulfur tetrafluoride|SF<sub>4</sub>]] }} }} '''Disulfur dichloride''' is the [[chemical compound]] with the [[Chemical formula|formula]] S<sub>2</sub>Cl<sub>2</sub>. Some alternative names for this compound are ''sulfur monochloride'' (the name implied by its [[empirical formula]], SCl), ''disulphur dichloride'' (British English Spelling) and ''sulphur monochloride'' (British English Spelling). S<sub>2</sub>Cl<sub>2</sub> has the structure implied by the formula Cl-S-S-Cl, wherein the angle between the Cl<sup>a</sup>-S-S and S-S-Cl<sup>b</sup> planes is 90°. This structure is referred to as gauche, and is akin to that for [[Hydrogen peroxide|H<sub>2</sub>O<sub>2</sub>]]. A different isomer of S<sub>2</sub>Cl<sub>2</sub> is S=SCl<sub>2</sub>; this isomer forms transiently when S<sub>2</sub>Cl<sub>2</sub> is exposed to UV-radiation. ==Synthesis and basic properties== Disulfur dichloride is an orange/yellow liquid that smokes in air due to reaction with water: ::2 S<sub>2</sub>Cl<sub>2</sub> + 2 H<sub>2</sub>O → SO<sub>2</sub> + 4 HCl + 3/8 S<sub>8</sub> It is synthesized by partial chlorination of elemental [[sulfur]]: ::S<sub>8</sub> + 4 Cl<sub>2</sub> → 4 S<sub>2</sub>Cl<sub>2</sub> ΔH = −58.2 kJ/mol Excess chlorine gives [[sulfur dichloride]]: ::S<sub>2</sub>Cl<sub>2</sub> + Cl<sub>2</sub> → 2 SCl<sub>2</sub> ΔH = −40.6 kJ/mol Both reactions are reversible, and upon standing, SCl<sub>2</sub> releases chlorine to revert to the disulfur dichloride. It has the ability to dissolve sulfur, which reflects in part the formation of polysulfanes: ::S<sub>2</sub>Cl<sub>2</sub> + n S → S<sub>2+n</sub>Cl<sub>2</sub> S<sub>2</sub>Cl<sub>2</sub> also arises from the chlorination of [[Carbon disulfide|CS<sub>2</sub>]] as in the synthesis of [[thiophosgene]]. ==Applications in synthesis== S<sub>2</sub>Cl<sub>2</sub> has been used to introduce C-S bonds. In the presence of [[Aluminium chloride|AlCl<sub>3</sub>]], S<sub>2</sub>Cl<sub>2</sub> reacts with benzene to give diphenyl sulfide: ::S<sub>2</sub>Cl<sub>2</sub> + C<sub>6</sub>H<sub>6</sub> → (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>S + 2 HCl + 1/8 S<sub>8</sub> [[Aniline]]s react with S<sub>2</sub>Cl<sub>2</sub> in the presence of NaOH via the so-called [[Herz reaction]] to give ''ortho''-aminothiophenolates. These species are precursors to thioindigo dyes. It is also used to prepare the [[sulfur mustard]] "gas" by reaction with ethylene: ::S<sub>2</sub>Cl<sub>2</sub> + 2 C<sub>2</sub>H<sub>4</sub> → (ClC<sub>2</sub>H<sub>4</sub>)<sub>2</sub>S + 1/8 S<sub>8</sub> ==References== {{Citationstyle|date=September 2007}} <references/> #Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5. #W. W. Hartman, L. A. Smith, and J. B. Dickey "Diphenylsulfide" Organic Syntheses, Coll. Vol. 2, p.242; Vol. 14, p.36. #R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4 #{{cite journal| author=Garcia-Valverde M., Torroba T.|title= Heterocyclic chemistry of sulfur chlorides - Fast ways to complex heterocycles |journal= European J. Org. Chem.|volume=4| pages= 849–861|year= 2006|doi= 10.1002/ejoc.200500786}} [[Category:Chlorides]] [[Category:Sulfur halides]] [[de:Dischwefeldichlorid]] [[fr:Chlorure de soufre]]