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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/3145

Title: Protection against peroxynitrite-mediated nitration reaction by intramolecularly coordinated diorganoselenides
Authors: KUMAR, S
SINGH, HB
WOLMERSHAUSER, G
Issue Date: 2006
Publisher: AMER CHEMICAL SOC
Citation: ORGANOMETALLICS,25(2)382-393
Abstract: A series of intramolecularly Se center dot center dot center dot X (X = N, O) coordinated diorganoselenides and sulfides are synthesized by using the heteroatom-directed lithiation route and characterized by multinuclear (H-1, C-13, Se-77) NMR, IR spectroscopy, and electrospray mass spectrometry (ES-MS). The intramolecular Se center dot center dot center dot O interactions in diorganoselenides 26-31 have been studied by multinuclear NMR studies in solution and in the solid state by single-crystal X-ray crystallography. The protection against peroxynitrite-mediated nitration reaction (PN assay) by diorganoselenides/-sulfides (with and without intramolecular coordination) has been evaluated. The PN assay data of diorganoselenides reveal that the selenides 20-22, having a basic amino group (sp(3)-N donor) in close proximity of selenium, are more active compared to the diorganoselenides 16-19, having an imino group (sp(2)-N donor), and also show much higher protective action than the unsubstituted diorganoselenides 14 and 15. The diorganoselenides 16-31 were oxidized to corresponding selenoxides 44-59. The redox properties of the selenoxides 13 and 44-59 have been investigated by cyclic voltammetry and potentiometric titration experiments. Two redox potentials for in situ-generated ferrocenyl selenoxides (50, 54-59) were observed. The reduction of selenoxides 13 and 48 to ebselen (2) and selenide 20 with benzenethiol (PhSH) was monitored by ES-MS.
URI: http://dx.doi.org/10.1021/om050353c
http://dspace.library.iitb.ac.in/xmlui/handle/10054/13953
http://hdl.handle.net/100/3145
ISSN: 0276-7333
Appears in Collections:Review

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