Organoselenium Chemistry

Organoselenium compounds are chemical compounds containing carbon-to-selenium chemical bonds. Organoselenium chemistry is the corresponding science exploring their properties and reactivity. Selenium belongs with oxygen and sulfur to the group 16 elements and similarities in chemistry are to be expected.

Selenium can exist with oxidation state -2, +2, +4, +6. Se(II) is the dominant form in organoselenium chemistry. Down the group 16 column, the bond strength becomes increasingly weaker (234 kJ/mol for the C–Se bond and 272 kJ/mol for the C–S bond) and the bond lengths longer (C–Se 198 pm, C–S 181 pm and C–O 141 pm). Selenium compounds are more nucleophilic than the corresponding sulfur compounds and also more acidic. The pKa values of XH2 are 16 for oxygen, 7 for sulfur and 3.8 for selenium. In contrast to sulfoxides, the corresponding selenoxides are unstable in the presence of β-protons and this property is utilized in many organic reactions of selenium, notably in selenoxide oxidations and in selenoxide eliminations. Organoselenium compounds are found at trace levels in ambient waters, soils and sediments.

The first organoselenium compound ever isolated was diethyl selenide in 1836.

Read more about Organoselenium ChemistryStructural Classification of Organoselenium Compounds, Organoselenium Compounds in Nature, Organoselenium Chemistry in Organic Synthesis

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Organoselenium Chemistry in Organic Synthesis - Selenoxide Eliminations
... The Grieco elimination is a similar selenoxide elimination using o-nitrophenylselenocyanate and tributylphosphine to cause the elimination of the elements of H2O. ...

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