Organoselenium chemistry | Wikipedia audio article
Channel: wikipedia tts
Date: 27/12/2018

This is an audio version of the Wikipedia Article:
https://en.wikipedia.org/wiki/Organoselenium_chemistry


00:01:59 1 Structural classification of organoselenium compounds
00:06:37 2 Organoselenium compounds in nature
00:08:08 2.1 Selenocysteine and selenomethionine
00:09:04 3 Organoselenium chemistry in organic synthesis
00:09:46 3.1 Vinylic selenides
00:11:30 3.2 Selenoxide oxidations
00:12:58 3.3 Selenoxide eliminations
00:14:11 3.4 Functionalization of olefins



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SUMMARY
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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 or chalcogens, 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.