UV-vis and IR spectroscopic characterization of diphenyl disulfide radical cation in acid zeolites and its rearrangement to thianthrenium radical cation
作者： Vicente Martí , Lorenzo Fernández , Vicente Fornés , Hermenegildo García , Heinz D. Roth
DOI: 10.1039/A806522E
关键词:
摘要: Adsorption of diphenyl disulfide (DPDS) from CH2Cl2 solutions onto acid zeolites at room temperature generated the “extended” radical cation, DPDS˙+. At loadings 3 wt%, oxidation to DPDS˙+ is essentially complete. Upon heating loaded zeolite 200 °C, adsorbed was converted into thianthrenium cation (TH˙+). Ab initio calculations B3LYP and HF levels using 6-31G* basis set suggest cyclization a disulfide-S,S-dication as reasonable rate-determining step conversion. Non-acidic devoid Lewis Bronsted sites (as determined by pyridine adsorption–desorption method) failed generate an extent detectable spectroscopically; these results support and/or being responsible for observed oxidation.
rsc.org
sci-hub.se 参考文章(31)
J WARD, The nature of active sites on zeolites IV. The influence of water on the acidity of X and Y type zeolites Journal of Catalysis. ,vol. 11, pp. 238- 250 ,(1968) , 10.1016/0021-9517(68)90037-7
Kimihisa Yamamoto, Eishun Tsuchida, Hiroyuki Nishide, Shu Yoshida, Y. ‐S. Park, Anodic Oxidation of Diphenyl Disulfides for Preparation of Oligo(p‐phenylene sulfide)s in Acidic Media Journal of The Electrochemical Society. ,vol. 139, pp. 2401- 2406 ,(1992) , 10.1149/1.2221239
E. Tsuchida, K. Yamamoto, H. Nishide, New Synthesis of Poly(Phenylenesulfide)S Through an Electron Transfer Journal of Macromolecular Science: Part A - Chemistry. ,vol. 27, pp. 1119- 1131 ,(1990) , 10.1080/00222339009349680
Adrian C. Archer, Peter A. Lovell, Formation of poly(1,4-phenylene sulfide) by solution polymerization of copper(I) 4- bromobenzenethiolate: experimental evidence for operation of single-electron transfer processes Polymer. ,vol. 36, pp. 4315- 4326 ,(1995) , 10.1016/0032-3861(95)92229-8
V. Ramamurthy, Jonathan V. Caspar, David R. Corbin, Generation, Entrapment, and Spectroscopic Characterization of Radical Cations of α,ω-Diphenyl Polyenes within the Channels of Pentasil Zeolites Journal of the American Chemical Society. ,vol. 113, pp. 594- 600 ,(1991) , 10.1021/JA00002A030
Geoffrey A. Ozin, John Godber, Intrazeolite metallocenes: chemistry, spectroscopy, and dynamics The Journal of Physical Chemistry. ,vol. 93, pp. 878- 893 ,(1989) , 10.1021/J100339A066
S. Płaza, R. Gruziński, Homogeneous and heterogeneous thermal decomposition of diphenyl disulphide Wear. ,vol. 194, pp. 212- 218 ,(1996) , 10.1016/0043-1648(95)06859-7
Judith Giordan, Hans Bock, Radical ions, 51. Oxidative Rearrangement of Diphenyl Disulfides to Thianthrenes Chemische Berichte. ,vol. 115, pp. 2548- 2559 ,(1982) , 10.1002/CBER.19821150718
A Corma, C Rodellas, V Fornes, Characterization of acid surfaces by adsorption of 2,6-dimethylpyridine Journal of Catalysis. ,vol. 88, pp. 374- 381 ,(1984) , 10.1016/0021-9517(84)90014-9
Christopher J. Rhodes, Electron paramagnetic resonance study of radical formation from cyclopentene and dimethylacetylene following adsorption onto H-mordenite Journal of the Chemical Society, Faraday Transactions. ,vol. 87, pp. 3179- 3184 ,(1991) , 10.1039/FT9918703179