Original scientific paper

Secondary Deuterium Isotope Effects in Some S N1 and E2 Reactions

S. Ašperger ; Department of Physical Chemistry, Institute »Ruder Boskovic«, Zagreb, and Department of Inorganic and Physical Chemistry, Faculty of Pharmacy, University of Zagreb, Zagreb, Croatia, Yugoslavia
N. Ilakovac ; Department of Physical Chemistry, Institute »Ruder Boskovic«, Zagreb, and Department of Inorganic and Physical Chemistry, Faculty of Pharmacy, University of Zagreb, Zagreb, Croatia, Yugoslavia
D . Pavlović ; Department of Physical Chemistry, Institute »Ruder Boskovic«, Zagreb, and Department of Inorganic and Physical Chemistry, Faculty of Pharmacy, University of Zagreb, Zagreb, Croatia, Yugoslavia

Abstract

An a-deuterium isotope effect kH/kn of 170/o was found in the
E 2 reaction of 2-phenylethyl-l,l-d2 bromide with sodium ethoxide
in ethanol. This supports the Streitwieser change-of-hybridization
theory and the associated explanation of the absence of such effects
in S N2 reactions as being due to the proximity of the incoming
group. The magnitude of the ~- and a-deuterium isotope effects in the
SNl and E2 reactions of some alkylsulphonium salts were determined
and compared with the isotope effects of the corresponding
alkyl-halides. An explanation for these differences is given.

Keywords

Hrčak ID:

208414

URI

https://hrcak.srce.hr/208414

Publication date:

15.5.1962.

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