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Issue 9, 1983
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A theoretical comparison of SN1 and SN2 reactions of saturated alkyl chlorides

Shinichi Yamabe,  Eiko Yamabe  and  Tsutomu Minato 

Abstract

The mechanistic difference between bimolecular (SN2) and unimolecular (SN1) nucleophilic substitutions of saturated alkyl chlorides is investigated with ab initio molecular orbital (MO) calculations. The t-butyl substrate undergoes early (almost spontaneous) C–Cl bond scission, which may give double OH–(reagent) co-ordination on the carbonium cation. However, the symmetrically solvated ion, which has been accepted as a stable intermediate for racemization, is found to be located at the energy maximum of the OH– exchange reaction. The origin of racemization in nucleophilic substitution is discussed on the basis of the calculated potential surface.

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Article type: Paper
DOI: 10.1039/P29830001881
Citation: J. Chem. Soc., Perkin Trans. 2, 1983,0, 1881-1884
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    A theoretical comparison of SN1 and SN2 reactions of saturated alkyl chlorides

    S. Yamabe, E. Yamabe and T. Minato, J. Chem. Soc., Perkin Trans. 2, 1983, 0, 1881
    DOI: 10.1039/P29830001881

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