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Enhanced Reactivity of RCCZ (R = H and Cl; Z = O, S, and Se) and the Influence of Leaving Group on the α-Effect in the E2 Reactions

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journal contribution
posted on 18.06.2010, 00:00 by Xi-Guang Wei, Xiao-Ming Sun, Xiao-Peng Wu, Yi Ren, Ning-Bew Wong, Wai-Kee Li
The enhanced reactivity exhibited by six pseudo-α-bases, RCCZ (R = H and Cl; Z = O, S, and Se) in gas-phase E2 reactions with ethyl chloride was examined at the G2(+) level. It is found that anomalous reactivity is observed despite the fact that these chalcogen bases do not possess adjacent lone-pair electrons. The influence of the halide leaving groups on the α-effect and the origin of the α-effect in the E2 reactions of ethyl halides are investigated and discussed.