Acta Phys. -Chim. Sin. ›› 1999, Vol. 15 ›› Issue (06): 500-505.doi: 10.3866/PKU.WHXB19990604

• ARTICLE • Previous Articles     Next Articles

Theoretical Study for the Mechanism of Electrophilic Addition to Alkenes Reactions

Zhou Zhi-Gang, Dai Qian-Huan   

  1. The Center of Environmental Science of Peking University,Beijing 100871|The Engineering Center of Chemistry and Biology of Beijing Polytechnic University,Beijing 100022
  • Received:1998-09-15 Revised:1998-12-01 Published:1999-06-15
  • Contact: Zhou Zhi-Gang


The potential intermediates of a series of electrophilic agents reacting with ethene have been computed with PM3 semiempirical method. The results show that the energy of the bridged structure intermediates is lower than that of the open structure intermediates as the central atom of electrophilic agents is the third, fourth or fifth periodic element, but higher as the central atom is the first or second periodic element. Thereby, the electrophilic agents with third, fourth or fifth periodic element as central atoms should give stereospecific and non-regionspecific products and those with first or second periodic element as central atoms should give non-stereospecific and regionspecific Products. It is well an accordance with experimental results. Meanwhile, the model of d-π and s-p-π coordination bond has been put forward to try to explain the molecular mechanism.

Key words: Electrophilic addition to alkene, Reaction mechanism, d-&pi, coordination bond, Stereochemistry, Regionchemistry, PM3