Dichlorodiselane
Selenium monochloride
Chemical compound
Selenium monochloride or diselenium dichloride is an inorganic compound with the formula Se2Cl2. Although a common name for the compound is selenium monochloride, reflecting its empirical formula, IUPAC does not recommend that name, instead preferring the more descriptive diselenium dichloride.
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| IUPAC name
Diselenium dichloride | |
Other names
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3D model (JSmol) |
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| ECHA InfoCard | 100.030.022  |
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CompTox Dashboard (EPA) |
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| Properties | |
| Se2Cl2 | |
| Molar mass | 228.84 g·mol−1 |
| Appearance | Reddish-brown oily liquid |
| Density | 2.7741 g/cm3 |
| Melting point | −85 °C (−121 °F; 188 K) |
| Boiling point | 127 °C (261 °F; 400 K) at 0.997 atm |
| insoluble | |
| Solubility in other solvents | Soluble in chloroform, carbon disulfide, and acetonitrile |
| −94.8·10−6 cm3/mol | |
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| H301, H311, H314, H331, H373, H410 | |
| P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diselenium dichloride is a reddish-brown, oily liquid that hydrolyses slowly. It exists in chemical equilibrium with SeCl2, SeCl4, chlorine, and elemental selenium.[1] Diselenium dichloride is mainly used as a reagent for the synthesis of Se-containing compounds.
Dielenium dichloride has the connectivity Cl−Se−Se−Cl. With a nonplanar structure, it has C2 molecular symmetry, similar to hydrogen peroxide and disulfur dichloride, which is referred to as gauche. The Se-Se bond length is 223 pm, and the Se-Cl bond lengths are 220 pm. The dihedral angle between the Cla−Se−Se and Se−Se−Clb planes is 87°.[2]
Early routes to diselenium dichloride involved chlorination of elemental selenium.[3] An improved method involves the reaction of a mixture of selenium, selenium dioxide, and hydrochloric acid:[4]
- 3 Se + SeO2 + 4 HCl → 2 Se2Cl2 + 2 H2O
A dense layer of diselenium dichloride settles from the reaction mixture, which can be purified by dissolving it in fuming sulfuric acid and reprecipitating it with hydrochloric acid. A second method for the synthesis involves the reaction of selenium with oleum and hydrochloric acid:[4]
The crude diselenium dichloride is removed via separatory funnel. Diselenium dichloride cannot be distilled without decomposition, even at reduced pressure.[4]
In acetonitrile solutions, it exists in equilibrium with SeCl2 and SeCl4.[5] Selenium dichloride degrades to diselenium dichloride after a few minutes at room temperature:[6]
- 3 SeCl2 → Se2Cl2 + SeCl4
Diselenium dichloride is an electrophilic selenizing agent, and thus it reacts with simple alkenes to give bis(β-chloroalkyl)selenide and bis(chloroalkyl)selenium dichloride. It converts hydrazones of hindered ketones into the corresponding selenoketones, the structural analogs of ketones whereby the oxygen atom is replaced with a selenium atom.[7] Finally, the compound has been used to introduce bridging selenium ligands between the metal atoms of some iron and chromium carbonyl complexes.[7]
- Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
- Kniep, Rüdiger; Körte, Lutz; Mootz, Dietrich (1 January 1983). "Kristallstrukturen von Verbindungen A2X2 (A = S, Se; X = Cl, Br)". Zeitschrift für Naturforschung B. 38 (1): 1–6. doi:10.1515/znb-1983-0102.
- Lenher, Victor; Kao, C. H. (1925). "The Preparation of Selenium Monochloride and Monobromide". Journal of the American Chemical Society. 47 (3): 772–774. doi:10.1021/ja01680a025.
- Fehér, F. (1963). "Diselenium Dichloride". In Brauer, G. (ed.). Handbook of Preparative Inorganic Chemistry. Vol. 1 (2nd ed.). New York: Academic Press. pp. 422–423.
- Lamoureux, Marc; Milne, John (1990). "Selenium chloride and bromide equilibria in aprotic solvents; a Se77 NMR study". Polyhedron. 9 (4): 589–595. doi:10.1016/S0277-5387(00)86238-5.
- Maaninen, Arto; Chivers, Tristram; Parvez, Masood; Pietikäinen, Jarkko; Laitinen, Risto S. (1999). "Syntheses of THF Solutions of SeX2(X = Cl, Br) and a New Route to Selenium Sulfides SenS8−n(n = 1−5): X-ray Crystal Structures of SeCl2(tht)2 and SeCl2·tmtu". Inorganic Chemistry. 38 (18): 4093–4097. doi:10.1021/ic981430h.
- Back, Thomas G.; Moussa, Ziad (2003). "Diselenium Dichloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00201. ISBN 0-471-93623-5.