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Base‐Catalysed H‐D Exchange in 1 ‐Methylthiolanium Iodide
Author(s) -
Barbarella G.,
Garbesi A.,
Fava A.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540135
Subject(s) - chemistry , carbanion , base (topology) , iodide , methylene , kinetics , medicinal chemistry , sulfur , computational chemistry , inorganic chemistry , organic chemistry , mathematical analysis , physics , mathematics , quantum mechanics
The kinetics of the base‐catalysed H/D exchange of the 1‐methylthiolanium cation in heavy water has been studied. Of the four α‐methylene protons, two exchange much faster than the other two, a result which requires that reprotonation of the carbanion intermediate occurs with retention of configuration. NMR. spectral analysis indicates that the protons undergoing faster exchange bear a trans relation to the lone‐pair on sulfur. This conclusion appears to conform to Wolfe 's theory on the stability of carbanions [3].