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Issue 61, 2014

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

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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


Submitted
08 May 2014
Accepted
02 Jul 2014
First published
08 Jul 2014

This article is Open Access

RSC Adv., 2014,4, 32415-32428
Article type
Review Article
Author version available

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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