Reactivity and mechanism of nucleophilic addition reaction of amine with alkene: A systematic DFT study

Authors

  • Zouhair Lakbaibi Molecular Modeling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P.O. Box 20, 24000 El Jadida, Morocco.
  • Adil Jaafar
  • Hicham Ben El Ayouchia
  • Mohamed Tabyaoui
  • Abdelghani Boussaoud

DOI:

https://doi.org/10.13171/mjc811902924zlhbea

Abstract

The reactivity and mechanism of the nucleophilic addition reaction of diethylamine 1 and 1-cyano-2-phenylvinyl methane sulfonate 2 have been studied for systematic understanding of this relevant organic transformation, using DFT calculations method at the B3LYP/6-311G(d,p) computational levels. Analysis of the conceptual DFT reactivity indices allows explaining the reactivity, and the calculated nucleophilic and electrophilic Parr functions at the reactive sites of reagents 1 and 2, respectively, allows explaining correctly the regioselectivity observed experimentally. The study has also been applied to predict the mechanism of amine with alkene. Interestingly, the study predicts a switch to a two-step mechanism due to the higher polar character of this zw-type nucleophilic addition reaction.

Author Biography

Zouhair Lakbaibi, Molecular Modeling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P.O. Box 20, 24000 El Jadida, Morocco.

Molecular Modeling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P.O. Box 20, 24000 El Jadida, Morocco.

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Published

2019-02-09

Issue

Vol. 8 No. 1 (2019)

Section

Theoretical Chemistry

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