Benzeneseleninic Acid

Back, Thomas G.

doi:10.1002/9780470842898.rb016.pub2

Cited by 1 publication

(1 citation statement)

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“…The chemical comparison between seleninic and sulfinic acids is analogous to that between SeO 2 and SO 2 , or between their hydrates, selenious acid (OSe(OH) 2 ) and sulfurous acid (OS(OH) 2 ). That is, seleninic acids are weak oxidizing agents (in fact seleninic anhydride has been proposed as a useful oxidant for many functional groups − ), whereas sulfinic acids are weak reducing agents. In a striking example of this (eq ), Kice reported that PhSeO 2 H and PhSO 2 H react with each other to reduce the former and oxidize the latter (eq ).…”

Section: Redox Propertiesmentioning

confidence: 99%

Why Nature Chose Selenium

2016

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The authors were asked by the Editors of ACS Chemical Biology to write an article titled "Why Nature Chose Selenium" for the occasion of the upcoming bicentennial of the discovery of selenium by the Swedish chemist Jöns Jacob Berzelius in 1817 and styled after the famous work of Frank Westheimer on the biological chemistry of phosphate [Westheimer, F. H. (1987) Why Nature Chose Phosphates, Science 235, 1173-1178]. This work gives a history of the important discoveries of the biological processes that selenium participates in, and a point-by-point comparison of the chemistry of selenium with the atom it replaces in biology, sulfur. This analysis shows that redox chemistry is the largest chemical difference between the two chalcogens. This difference is very large for both one-electron and two-electron redox reactions. Much of this difference is due to the inability of selenium to form π bonds of all types. The outer valence electrons of selenium are also more loosely held than those of sulfur. As a result, selenium is a better nucleophile and will react with reactive oxygen species faster than sulfur, but the resulting lack of π-bond character in the Se-O bond means that the Se-oxide can be much more readily reduced in comparison to S-oxides. The combination of these properties means that replacement of sulfur with selenium in nature results in a selenium-containing biomolecule that resists permanent oxidation. Multiple examples of this gain of function behavior from the literature are discussed.

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Section: Redox Propertiesmentioning

confidence: 99%