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

Zouhair Lakbaibi, Adil Jaafar, Hicham Ben El Ayouchia, Mohamed Tabyaoui, Abdelghani Boussaoud


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.

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- T. E. Müller, M. Beller, Chemical Reviews, 1998, 98, 675-704.

- Kai C. Hultzsch, Organic and Biomolecular Chemistry, 2005, 3, 1819-1824.

- T. E. Muller, K. C, Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev, 2008, 108, 3795-3892.

- C. R. Brindaban, S. D. Suvendu, H. Alakananda, 2002, 5, 76-81.

- G. R. Westerhof, R. E. Ploemacher, A. Boudewijn, I. Blokland, J. H. Dillingh, A.T. Mc Gown, J. A. Hadfield, M. J. Dawson, J. D. Down, CANCER RESEARCH, 2000, 60, 5470-5478.

- Lin. Tai-Shun, H. Prusoff. William, J. Med. Chem, 1978, 21, 109-112.

- F. Fraser. Fleming, Lihua Yao, P.C. Ravikumar, Lee Funk, C. Shook. Brian, J Med Chem, 2010, 53, 7902- 7917.

- P. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev, 2003, 103, 1793-1874.

- A. D. Becke, J. Chem. Phys, 1993, 98, 5648-5652.

- C. Lee, W. Yang, R. G. Parr, Phys Rev B, 1988, 37, 785-789.

- W. J. Hehre, L. Radom, P. Schleyer, J. A. Pople, J. Comput. Chem, 1986, 7, 379-383.

- C. Gonzales, H. B. Schlegel, J. Chem. Phys, 1989, 90, 2154-2161.

- J. Tomasi, M. Persico, Chem Rev, 1994, 94, 2027-2094.

- B. Y. Simkin, I. Sheikhet, Ellis Horwood, London, 1995.

- E. Cances, B. Mennucci, J. Tomasi. J Chem Phys, 1997, 107, 3032-3041.

- V. Barone, M. Cossi, J. Tomasi. J Comput Chem, 1998, 19, 404-417.

- L. R. Domingo, RSC Adv, 2014, 4, 32415-32428.

- A. Benallou, Z. Lakbaibi, H. Garmes, H. El Alaoui EL Abdallaoui, J. Fluorine. Chem., 2019, 219, 79-91.

- M. J. Frisch et al., GAUSSIAN 09, Revision E. 01, Gaussian Inc., Wallingford CT, 2009.

- P. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev, 2003, 103, 1793-1874.

- Z. Lakbaibi, H. Abou EL Makarim, M. Tabyaoui, A. EL Hajbi, Journal of Materials and Environmental Science, 2016, 8, 99-115.

- Z. Lakbaibi, H. Abou EL Makarim, M. Tabyaoui, A. EL Hajbi, Moroccan Journal of Chemistry, 2016, 4, 437-453.

- L. R. Domingo, M. R. Gutérrez, P. Pérez, J. Org. Chem, 2018, 83, 2182-2197.

- L. R. Domingo, M. J. Aurell, P. Pérez, R. Contreras, Tetrahedron, 2002, 58, 4417-4423.

- L. R. Domingo, M. R. Gutiérrez, B. Silvi, P. Pérez, Chem. Eur. J, 2018, 9, 1107-1120.



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