Issue 22, 2022

Exploring the reactivity of L-tellurocystine, Te-protected tellurocysteine conjugates and diorganodiselenides towards hydrogen peroxide: synthesis and molecular structure analysis

Abstract

The oxidation reaction of L-tellurocystine, [Te2{CH2CH(NH3+)COO}2] (4) with H2O2 in the presence of HBr resulted in the formation of cyclic, zwitterionic organotellurolate(IV) species, namely [Te{CH2CH(NH3+)COO}(Br)3] (5). The H2O2 oxidation of Te-protected tellurocysteine derivatives [RTe{CH2CH(NH2)COOH}] [R = C6H5 (6) and 4-MeC6H4 (7)] in the presence of HCl resulted in the formation of chlorotellurane species [(C6H5)Te{CH2CH(NH3+)COOH}(Cl)2]Cl (8) and [(4-MeC6H5)Te{CH2CH(NH3+)COO}(Cl)]Cl (9), respectively. The oxidation reaction of diorganodiselenides R2Se2 [R = 4-MeC6H4 (10), R = 4-OMeC6H4 (11), R = 3,4-Me2C6H3 (12) and R = 2,4,6-Me3C6H2 (13)] with H2O2 afforded homoleptic diorganoselenones R2SeO2 [R = 4-MeC6H4 (14), R = 4-OMeC6H4 (15), R = 3,4-Me2C6H3 (16) and R = 2,4,6-Me3C6H2 (17)], respectively. The synthesized compounds were thoroughly characterized by multinuclear NMR (1H, 13C, 125Te/77Se), FT-IR spectroscopy, ESI-MS and elemental analysis. The molecular structures of the compounds were determined by single crystal X-ray diffraction studies.

Graphical abstract: Exploring the reactivity of L-tellurocystine, Te-protected tellurocysteine conjugates and diorganodiselenides towards hydrogen peroxide: synthesis and molecular structure analysis

Supplementary files

Article information

Article type
Paper
Submitted
27 Feb 2022
Accepted
27 Mac 2022
First published
30 Mac 2022

New J. Chem., 2022,46, 10550-10559

Exploring the reactivity of L-tellurocystine, Te-protected tellurocysteine conjugates and diorganodiselenides towards hydrogen peroxide: synthesis and molecular structure analysis

A. Tripathi, R. Deka, R. J. Butcher, D. R. Turner, G. B. Deacon and H. B. Singh, New J. Chem., 2022, 46, 10550 DOI: 10.1039/D2NJ00997H

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