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Organoselenium chemistry is the science exploring the properties and reactivity of organoselenium compounds, chemical compounds containing carbon-to-selenium chemical bonds. [ 1 ] [ 2 ] [ 3 ] Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected.
Selenium forms two oxides: selenium dioxide (SeO 2) and selenium trioxide (SeO 3). Selenium dioxide is formed by the reaction of elemental selenium with oxygen: [5] + It is a polymeric solid that forms monomeric SeO 2 molecules in the gas phase. It dissolves in water to form selenous acid, H 2 SeO 3.
Selenium monochloride or diselenium dichloride is an inorganic compound with the formula Se 2 Cl 2. 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.
Selenium is found in metal sulfide ores, where it substitutes for sulfur. Commercially, selenium is produced as a byproduct in the refining of these ores. Minerals that are pure selenide or selenate compounds are rare. The chief commercial uses for selenium today are glassmaking and pigments. Selenium is a semiconductor and is used in photocells.
Carbonyl selenide can be produced by treating selenium with carbon monoxide in the presence of amines. [3]It is used in organoselenium chemistry as a means of incorporating selenium into organic compounds, e.g. for the preparation of selenocarbamates (O-selenocarbamates R−O−C(=Se)−NR'R" and Se-selenocarbamates, R−Se−C(=O)−NR'R", where R is organyl and R' and R" are any group ...
Carbon dioxide – CO 2; Carbon disulfide – CS 2; Carbon monoxide – CO; Carbon tetrabromide – CBr 4; Carbon tetrachloride – CCl 4; Carbon tetrafluoride – CF 4; Carbon tetraiodide – CI 4; Carbonic acid – H 2 CO 3; Carbonyl chloride – COCl 2; Carbonyl fluoride – COF 2; Carbonyl sulfide – COS; Carboplatin – C 6 H 12 N 2 O 4 Pt
Following rearrangement and loss of water, a second equivalent of water attacks the alpha position. Red amorphous selenium is liberated in the final step to give the 1,2-dicarbonyl product. [8] [9]: 4331 Allylic oxidation using selenium-dioxide proceeds via an ene reaction at the electrophilic selenium center.
The original synthesis involved the redistribution reaction of selenium dioxide and selenium tetrachloride. Pure selenium oxydichloride autoionizes to a dimer: [4] SeOCl 2 ↔ (SeO) 2 Cl + 3 + Cl −. The SeOCl 2 is generally a labile Lewis acid and solutions of sulfur trioxide in SeOCl 2 likely form [SeOCl] + [SO 3 Cl] − the same way. [5]