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Different Approaching Directions of σ and π Nucleophiles to the Sulfur Atom of Thiiranium and Thiirenium Ions
Author(s) -
Modena Giorgio,
Pasquato Lucia,
Lucchini Vittorio
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000218)6:4<589::aid-chem589>3.0.co;2-j
Subject(s) - sulfur , nucleophile , ion , atom (system on chip) , chemistry , computational chemistry , computer science , organic chemistry , parallel computing , catalysis
Conflicting directions? Recently, L. Radom et al. reported a theoretical investigation on the nucleophilic attack of ethylene or acetylene to the sulfur atom of unsubstituted thiiranium and thiirenium ions (T. I. Sølling, S. B. Wild, L. Radom, Chem. Eur. J. 1999 , 5 , 509). They found two transition states that corresponded to the addition of the double or triple bond along the x or z direction, whereas our experimental results show that nucleophilic attack of dialkyl disulfide to the sulfur atom occurs along the y direction. Herein we give an explanation for the apparent discrepancies of these results.