Title
The bonding nature of some simple sigmatropic transition states from the topological analysis of the electron localization function
Date Issued
28 November 2002
Access level
metadata only access
Resource Type
journal article
Author(s)
Universidad de Chile
Abstract
It is shown that the topological analysis of the electron localization function (ELF), a measure of the local Pauli repulsion, is a useful tool to describe the bonding nature of transition structures of simple pericyclic processes. In this work, we have revisited the [1s,3a]hydrogen, [1a,3s]methyl, and [1a,3s]fluorine simple sigmatropic rearrangements in the allyl system. Results based on the integrated densities over the ELF basins and their related properties at the B3LYP/6-311++G(d,p) level of theory showed explicitly a delocalized structure for the antarafacial (Cs hydrogen rearrangement, a two radical interaction for the methyl suprafacial (C2) migration, and a pair-ion interaction for the fluorine suprafacial (Cs) transfer. Results on these well-studied systems confirm the topological analysis of the ELF as a useful descriptor for the study of bonding structure of pericyclic transition states. In this context, the ELF analysis is shown to be a complementary value to the Woodward-Hoffmann rules, which provide an orbital symmetry basis of understanding.
Start page
11533
End page
11539
Volume
106
Issue
47
Language
English
OCDE Knowledge area
Química analítica
Bioquímica, Biología molecular
Scopus EID
2-s2.0-0037191811
Source
Journal of Physical Chemistry A
ISSN of the container
10895639
Sources of information:
Directorio de Producción Científica
Scopus