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{{chembox |
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| verifiedrevid = 389337400 |
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|verifiedrevid = 444677336 |
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| Name = Selenium monochloride |
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|Name = Diselenium dichloride |
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|ImageFile =Diselenium_dichloride.jpg |
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|ImageSize = 132 |
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| IUPACName = Selenium monochloride |
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|IUPACName = Diselenium dichloride |
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| OtherNames = Dichlorodiselenide, Diselenium dichloride, Selenium chloride, 1,2-dichlorodiselane |
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|OtherNames = {{ubl|1,2-Dichlorodiselane|Dichlorodiselane|Dichlorodiselenide|Selenium chloride|Selenium monochloride}} |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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|CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 10025-68-0 |
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|CASNo = 10025-68-0 |
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| RTECS = |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = |
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|ChemSpiderID = 59591 |
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}} |
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|EINECS = 233-037-8 |
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| Section2 = {{Chembox Properties |
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|PubChem = 66206 |
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| Formula = Se<sub>2</sub>Cl<sub>2</sub> |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| MolarMass = 228.83 g/mol |
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|UNII = 2A5292FC4P |
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| Appearance = Reddish-brown oily liquid |
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|SMILES = ClCl |
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| Density = 2.7741 g/cm<sup>3</sup> |
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|InChI = 1/Cl2Se2/c1-3-4-2 |
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| Solubility = insoluble; sol in CHCl<sub>3</sub>, CS<sub>2</sub>, MeCN |
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|InChIKey = VIEXQFHKRAHTQS-UHFFFAOYAC |
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| SolubleOther = Soluble in dry chloroform and carbon disulfide |
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|StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| MeltingPt = -85 °C (223.15 K) |
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|StdInChI = 1S/Cl2Se2/c1-3-4-2 |
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| BoilingPt = 127 °C at 0.997 atm (400.15 K at 0.997 atm) |
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|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChIKey = VIEXQFHKRAHTQS-UHFFFAOYSA-N |
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| Section3 = {{Chembox Structure |
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|Section2={{Chembox Properties |
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|Formula = {{chem2|Se2Cl2}} |
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| CrystalStruct = |
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|Se=2|Cl=2 |
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|Appearance = Reddish-brown oily liquid |
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|Density = 2.7741 g/cm<sup>3</sup> |
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|Solubility = insoluble |
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| Section7 = {{Chembox Hazards |
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|SolubleOther = Soluble in chloroform, carbon disulfide, and acetonitrile |
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|Solvent=other solvents |
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|MeltingPtC = -85 |
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|BoilingPtC = 127 |
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|BoilingPt_notes = at 0.997 atm |
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| RPhrases = 23/24/25-34 |
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|MagSus = −94.8·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| SPhrases = 22-26-36/37/39-45 |
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| FlashPt = |
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| Section8 = {{Chembox Related |
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|Section3={{Chembox Hazards |
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|GHSPictograms = {{GHS05}}{{GHS06}}{{GHS08}}{{GHS09}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|301|311|314|331|373|410}} |
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|PPhrases = {{P-phrases|260|261|264|270|271|273|280|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|311|312|314|321|322|330|361|363|391|403+233|405|501}} |
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'''Selenium monochloride''' or '''diselenium dichloride''' is an ] with the formula {{chem2|Se2Cl2|auto=1}}. Although a common name for the compound is selenium monochloride, reflecting its ], ] does not recommend that name, instead preferring the more descriptive diselenium dichloride. |
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'''Selenium monochloride''' is an ] with the formula Se<sub>2</sub>Cl<sub>2</sub>. Although it is called selenium monochloride, a more descriptive name might be diselenium dichloride. It is a reddish-brown, oily liquid that is hydrolyses slowly. It exists in ] with SeCl<sub>2</sub>, SeCl<sub>4</sub>, ], and elemental ].<ref>{{Greenwood&Earnshaw2nd}}</ref> Selenium monochloride is mainly used as a ] for the synthesis of Se-containing compounds. |
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Diselenium dichloride is a reddish-brown, oily liquid that hydrolyses slowly. It exists in ] with ], ], ], and elemental ].<ref>{{Greenwood&Earnshaw2nd}}</ref> Diselenium dichloride is mainly used as a ] for the synthesis of Se-containing compounds. |
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==Structure and properties== |
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==Structure and properties== |
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Selenium monochloride exhibits C<sub>2</sub> ], similar to ]. The ] of the Se-Se bond is predicted to be 2.253 Å and the Se-Cl bonds are both 2.227 Å.<ref name=Prascher>Prascher, Brian P.; Wilson, Angela K. A Computational Study of Dihalogen-μ-Dichalcogenides: XAAX (X = F, Cl, Br; A = S, Se). ''Journal of Molecular Structure''. 2007, ''814'', 1-10.{{doi|10.1016/j.theochem.2007.02.040}}</ref> |
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Dielenium dichloride has the connectivity {{chem2|Cl\sSe\sSe\sCl}}. With a nonplanar structure, it has C<sub>2</sub> ], similar to ] and ], which is referred to as ]. The Se-Se ] is 223 ], and the Se-Cl bond lengths are 220 pm. The ] between the {{chem2|Cl^{''a''}\sSe\sSe}} and {{chem2|Se\sSe\sCl^{''b''}|}} planes is 87°.<ref>{{cite journal |last1=Kniep |first1=Rüdiger |last2=Körte |first2=Lutz |last3=Mootz |first3=Dietrich |title=Kristallstrukturen von Verbindungen A<sub>2</sub>X<sub>2</sub> (A = S, Se; X = Cl, Br) |journal=Zeitschrift für Naturforschung B |date=1 January 1983 |volume=38 |issue=1 |pages=1–6 |doi=10.1515/znb-1983-0102 |doi-access=free}}</ref> |
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In ] solutions, it exists in equilibrium with SeCl<sub>2</sub> and SeCl<sub>4</sub>.<ref>Marc Lamoureux and John Milne "Selenium chloride and bromide equilibria in aprotic solvents; a <sup>77</sup>Se NMR study" Polyhedron 1990, Volume 9, pp. 589-595. {{doi|10.1016/S0277-5387(00)86238-5}}</ref> |
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==Preparation== |
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==Preparation== |
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Selenium monochloride was originally produced by the chlorination of selenium.<ref>J. J. Berzelius, Annales de chimie et de physique 1818, vol. 9, 225. See also Kao, C. H.; Lenher, V. The Preparation of Selenium Monochloride and Monobromide, ''J. Am. Chem. Soc.'', 1925, ''48'', 772-774. {{DOI|10.1021/ja01680a025}}</ref> An improved method involves the reaction of a mixture of selenium, selenium dioxide, and hydrochloric acid:<ref name=Feher>Fehér, F. "Diselenium Dichloride". In ''Handbook of Preparative Inorganic Chemistry''; Brauer, G., Ed.; Academic Press: New York, 1963; Vol. 1; p 422-433.</ref> |
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Early routes to diselenium dichloride involved ] of elemental ].<ref>{{cite journal |doi=10.1021/ja01680a025|title=The Preparation of Selenium Monochloride and Monobromide|journal=Journal of the American Chemical Society|volume=47|issue=3|pages=772–774|year=1925|last1=Lenher|first1=Victor|last2=Kao|first2=C. H.}}</ref> An improved method involves the reaction of a mixture of selenium, ], and ]:<ref name="Feher">{{Cite book |last=Fehér |first=F. |chapter-url=https://archive.org/details/Handbook_of_Preparative_Inorganic_Chemistry_1_2_Brauer/page/n447 |title=Handbook of Preparative Inorganic Chemistry |publisher=Academic Press |year=1963 |editor-last=Brauer |editor-first=G. |edition=2nd |volume=1 |location=New York |pages=422-423 |chapter=Diselenium Dichloride}}</ref> |
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:3 Se + SeO<sub>2</sub> + 4 HCl → 2 Se<sub>2</sub>Cl<sub>2</sub> + H<sub>2</sub>O |
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:{{chem2|3 Se + SeO2 + 4 ] → 2 Se2Cl2 + 2 H2O}} |
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A dense layer of selenium monochloride settles from the reaction mixture, which can be purified by dissolving it in fuming ] and reprecipitating it with ]. A second method for the synthesis involves the reaction of selenium with ] and hydrochloric acid:<ref name=Feher/> |
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A dense layer of diselenium dichloride settles from the reaction mixture, which can be purified by dissolving it in fuming ] and reprecipitating it with hydrochloric acid. A second method for the synthesis involves the reaction of selenium with ] and hydrochloric acid:<ref name=Feher/> |
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:2 Se + 2 SO<sub>3</sub> + 3 HCl → Se<sub>2</sub>Cl<sub>2</sub> + H<sub>2</sub>SO<sub>3</sub> + SO<sub>2</sub>(OH)Cl |
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:{{chem2|2 Se + 2 ] + 3 HCl → Se2Cl2 + ] + H2O + ]}} |
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The crude diselenium dichloride is removed via separatory funnel. Diselenium dichloride cannot be distilled without decomposition, even at reduced pressure.<ref name=Feher/> |
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The crude selenium monochloride product is collected via distillation. |
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In ] solutions, it exists in equilibrium with {{chem2|SeCl2}} and {{chem2|SeCl4}}.<ref>{{cite journal |last1=Lamoureux |first1=Marc |last2=Milne |first2=John |year=1990 |title=Selenium chloride and bromide equilibria in aprotic solvents; a Se77 NMR study |journal=Polyhedron |volume=9 |issue=4 |pages=589–595 |doi=10.1016/S0277-5387(00)86238-5}}</ref> ] degrades to diselenium dichloride after a few minutes at room temperature:<ref>{{cite journal |journal=Inorganic Chemistry|year=1999|volume=38|issue=18|pages=4093–4097|doi=10.1021/ic981430h|title=Syntheses of THF Solutions of SeX<sub>2</sub>(X = Cl, Br) and a New Route to Selenium Sulfides Se<sub>''n''</sub>S<sub>8−''n''</sub>(''n'' = 1−5): X-ray Crystal Structures of SeCl<sub>2</sub>(tht)<sub>2</sub> and SeCl<sub>2</sub>·tmtu|last1=Maaninen|first1=Arto|last2=Chivers|first2=Tristram|last3=Parvez|first3=Masood|last4=Pietikäinen|first4=Jarkko|last5=Laitinen|first5=Risto S.}}</ref> |
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:{{chem2|3 SeCl2 → Se2Cl2 + SeCl4}} |
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==Reactions== |
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==Reactions== |
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Selenium monochloride is an electrophilic selenizing agent, and thus it reacts with simple ]s to give bis(''β''-chloroalkyl)selenide and bis(chloroalkyl)selenium dichloride.<ref name=Back>Back, Thomas G.; Moussa, Ziad "Diselenium Dichloride" ''Encyclopedia of Reagents for Organic Synthesis'' 2003 {{DOI|10.1002/047084289X.rn00201}}</ref> It converts ]s of hindered ketones into the corresponding ], the structural analogs of ketones whereby the oxygen atom is replaced with a selenium atom.<ref name=Back/> Finally, the compound has been used to introduce bridging selenium ligands between the metal atoms of some iron and chromium carbonyl complexes.<ref name=Back/> |
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Diselenium dichloride is an electrophilic selenizing agent, and thus it reacts with simple ]s to give bis(''β''-chloroalkyl)selenide and bis(chloroalkyl)selenium dichloride. It converts ]s of hindered ketones into the corresponding ]s, the structural analogs of ketones whereby the oxygen atom is replaced with a selenium atom.<ref name=Back/> Finally, the compound has been used to introduce bridging selenium ligands between the metal atoms of some iron and chromium carbonyl complexes.<ref name=Back>{{cite encyclopedia |author=Back, Thomas G. |author2=Moussa, Ziad|chapter=Diselenium Dichloride|title=Encyclopedia of Reagents for Organic Synthesis|year=2003 |doi=10.1002/047084289X.rn00201|isbn=0-471-93623-5}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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<references/> |
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{{Selenium compounds}} |
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{{Selenium compounds}} |
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{{Chlorides}} |
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