Hydrolysis of an isolable selenoseleninate under acidic and alkaline conditions

Ishii, Akihiko; Takahashi, Takeshi; Nakayama, Juzo

doi:10.1002/hc.1032

Cited by 13 publications

(2 citation statements)

References 26 publications

(31 reference statements)

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“…(6) under the conditions. This result is in harmony with the fact that nucleophilicity of a selenol toward a selenium atom in a diselenide increases greatly in the selenolate ion form (RSe − ) compared with the selenol form (RSeH) [6,15,16]. An attempt to trap 3 with triphenyltin chloride under the basic conditions was unsuccessful.…”

Section: (4)supporting

confidence: 66%

Synthesis and hydrolysis ofp-toluoyl and acetyl 9-triptycyl diselenides: A study on generation of triptycene-9-selenenoselenoic acid

2005

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Section: (4)supporting

confidence: 66%

Synthesis and hydrolysis ofp-toluoyl and acetyl 9-triptycyl diselenides: A study on generation of triptycene-9-selenenoselenoic acid

2005

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“…Besides, it is worth mentioning that, according to published data, in the presence of excess hydrogen peroxide, the diselenides are further oxidized to selenoseleninate derivatives (-Se(O)-Se-), which are unstable under basic conditions [ 28 , 29 , 30 ]. These compounds are hydrolyzed to seleninic acid (RSeO 2 H) and selenol (RSeH), while, in acidic environments, selenenic acid (RSeOH) is formed [ 31 ]. Our efforts to confirm such transformation pathways have been unsuccessful, probably due to the low stability of the selenoseleninate derivative.…”

Section: Discussionmentioning

confidence: 99%

Different Oxidation Pathways of 2-Selenouracil and 2-Thiouracil, Natural Components of Transfer RNA

Kulik

Sadowska

Wielgus

et al. 2020

IJMS

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Sulfur- and selenium-modified uridines present in the wobble position of transfer RNAs (tRNAs) play an important role in the precise reading of genetic information and tuning of protein biosynthesis in all three domains of life. Both sulfur and selenium chalcogens functionally operate as key elements of biological molecules involved in the protection of cells against oxidative damage. In this work, 2-thiouracil (S2Ura) and 2-selenouracil (Se2Ura) were treated with hydrogen peroxide at 1:0.5, 1:1, and 1:10 molar ratios and at selected pH values ranging from 5 to 8. It was found that Se2Ura was more prone to oxidation than its sulfur analog, and if reacted with H2O2 at a 1:1 or lower molar ratio, it predominantly produced diselenide Ura-Se-Se-Ura, which spontaneously transformed to a previously unknown Se-containing two-ring compound. Its deselenation furnished the major reaction product, a structure not related to any known biological species. Under the same conditions, only a small amount of S2Ura was oxidized to form Ura-SO2H and uracil (Ura). In contrast, 10-fold excess hydrogen peroxide converted Se2Ura and S2Ura into corresponding Ura-SeOnH and Ura-SOnH intermediates, which decomposed with the release of selenium and sulfur oxide(s) to yield Ura as either a predominant or exclusive product, respectively. Our results confirmed significantly different oxidation pathways of 2-selenouracil and 2-thiouracil.

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Selenium and Tellurium (1,2,3)‐Oxygen‐containing Acids and Derivatives

Drabowicz

Krasowska

2011

Patai's Chemistry of Functional Groups

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The chapter presents the advances in the chemistry of oxoacids of selenium and tellurium and their derivatives, which have emerged in recent years (mostly after 1998) based on the division of the discussed compounds into particular subclasses arising from the oxidation state of a central chalcogen atom. It begins with a brief discussion on the nature of bonding between the chalcogen and oxygen atoms. Next this chapter presents for the first time all the available data on basic synthetic protocols leading to alkane (arene) oxoacids of selenium and tellurium, and the acid halides, esters and amides derived from them. A brief discussion on their structure and reactivity is also included. The derivatives are presented in the following order: (a) divalent, dicoordinated selenenic and tellurenic acids, RChOH (ChSe or Te), and their derivatives; (b) tetravalent, tricoordinated seleninic and tellurinic acids, RCh(O)OH, and their derivatives RCh(O)L (ChSe or Te; LX, OR, NR 1 R 2 ); (c) hexavalent, tetraacoordinated selenonic and telluronic acids, RCh(O) 2 OH, and their derivatives RCh(O) 2 L (ChSe or Te; LX, OR, NR 1 R 2 ).

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Hydrolysis of an isolable selenoseleninate under acidic and alkaline conditions

Cited by 13 publications

References 26 publications

Synthesis and hydrolysis ofp-toluoyl and acetyl 9-triptycyl diselenides: A study on generation of triptycene-9-selenenoselenoic acid

Synthesis and hydrolysis ofp-toluoyl and acetyl 9-triptycyl diselenides: A study on generation of triptycene-9-selenenoselenoic acid

Different Oxidation Pathways of 2-Selenouracil and 2-Thiouracil, Natural Components of Transfer RNA

Selenium and Tellurium (1,2,3)‐Oxygen‐containing Acids and Derivatives

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