Issue 61, 2014

A new C–C bond formation model based on the quantum chemical topology of electron density

Abstract

ELF topological analyses of bonding changes in non-polar, polar and ionic organic reactions involving the participation of C[double bond, length as m-dash]C(X) double bonds make it possible to establish a unified model for C–C bond formation. This model is characterised by a C-to-C coupling of two pseudoradical centers generated at the most significant atoms of the reacting molecules. The global electron density transfer process that takes place along polar and ionic reactions favours the creation of these pseudoradical centers at the most nucleophilic/electrophilic centers of the reacting molecules, decreasing activation energies. The proposed reactivity model based on the topological analysis of the changes in electron density throughout a reaction makes it possible to reject the frontier molecular orbital reactivity model based on the analysis of molecular orbitals.

Graphical abstract: A new C–C bond formation model based on the quantum chemical topology of electron density

Article information

Article type
Review Article
Submitted
08 mei 2014
Accepted
02 jul 2014
First published
08 jul 2014
This article is Open Access
Creative Commons BY license

RSC Adv., 2014,4, 32415-32428

A new C–C bond formation model based on the quantum chemical topology of electron density

L. R. Domingo, RSC Adv., 2014, 4, 32415 DOI: 10.1039/C4RA04280H

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