Base‐Catalysed H‐D Exchange in 1 ‐Methylthiolanium Iodide | Zendy

Barbarella G. | Zendy; Garbesi A. | Zendy; Fava A. | Zendy

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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].

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