A DFT study of the role of the Mg complex formation on the mechanism of the 1,3-dipolar cycloadditions of benzonitrile oxides with acryloylpyrazolidinone

  • Domingo L
  • Aurell M
  • Jalal R
 et al. 
  • 3


    Mendeley users who have this article in their library.
  • 9


    Citations of this article.


The role of the Mg complex formation on the mechanism, the reaction rate and regioselectivity of the 1,3-dipolar cycloaddition (13DC) reactions of benzonitrile oxides (BNOs) towards electron-deficient acryloylpyrazolidinones has been theoretically studied using DFT methods at the 6-31G* level. These 13DC reactions have asynchronous concerted mechanism with a non-polar character. These cycloadditions present a slight 5-regioselectivity induced by a steric repulsion between the phenyl substituent of the BNOs and the pyrazolidinone appendage present on the acryloyl derivative, which increases with the formation of the bulky Mg-acryloylpyrazolidinone complex. The present DFT study points out that the coordination of the Mg2+to the two oxygen atoms of the acryloyl derivative does not produce a discernible change in the mechanism and the reaction rate as a consequence of the non-polar character of these cycloadditions, but produces a regio- and stereoselective induction because of the hindrance produced by the bulk chiral magnesium complex. In this study the solvent effect is also examined. © 2009 Elsevier B.V. All rights reserved.

Author-supplied keywords

  • 1,3-Dipolar cycloadditions
  • Benzonitrile oxides
  • Density functional theory
  • Magnesium Lewis acid
  • Molecular mechanism

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document


Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free