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Mechanisms of the reaction between benzonitrile and 4‐octyne catalyzed by Ni(PMe 3 ) 2 : A theoretical investigation
Author(s) -
Zhou DaGang,
Wang Peng
Publication year - 2019
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3932
Subject(s) - benzonitrile , chemistry , density functional theory , reductive elimination , catalysis , polarizable continuum model , computational chemistry , yield (engineering) , metal , solvent , medicinal chemistry , solvent effects , organic chemistry , thermodynamics , physics
The reaction mechanisms of benzonitrile and 4‐octyne catalyzed by Ni(PMe 3 ) 2 have been investigated using density functional theory (DFT) method at the B3LYP/6‐31+G(d,p) level, and the conductor‐like polarizable continuum model (CPCM) model was applied to simulate the solvent effect. The computational results suggest that benzonitrile has three possible paths to generate metallic intermediate. Then insertion and reductive elimination reactions happen between the metallic intermediate and 4‐octyne to yield the final product (Z)‐3‐phenyl‐2‐propyl‐2‐hexenenitrile. The analysis of frontier molecular orbital and electron density difference could help to reveal the substance of this reaction. And the results could provide valuable insights into these types of interactions and related ones.