Core electron binding energy (CEBE) shifts applied to structure activity relationship (SAR) analysis of neolignans

M Cristina A Costa,Yuji Takahata

doi:10.1590/s0103-50532002000600012

M Cristina A Costa, Yuji Takahata

Open Access

https://doi.org/10.1590/s0103-50532002000600012

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Abstract

Core electron binding energy shifts (DCEBE's) and CEBE of carbon atoms calculated with the semi empirical HAM/3 method were shown to serve as a useful descriptor for SAR analysis of six neolignans studied. Using five selected DCEBE's of carbon atoms in the two phenyl rings of the compounds, the compounds were well separated by HCA, PCA, KNN and SIMCA methods.

Highlights

The choice of molecular descriptors is one of the most crucial parts in the work of SAR/QSAR
Some descriptors that can be calculated by quantum mechanical methods have been recognized as useful in QSAR
One of our objectives is to look for more useful descriptors than far used, employing mainly quantum mechanical and/or other theoretical and computational methods

Summary

Introduction

The choice of molecular descriptors is one of the most crucial parts in the work of SAR/QSAR. Many descriptors have been suggested and employed. Many of them are successful and well accepted. Some descriptors that can be calculated by quantum mechanical methods have been recognized as useful in QSAR. There still remains room to search for alternative and/or better descriptors than those in use, especially those descriptors that can be evaluated theoretically. One of our objectives is to look for more useful descriptors than far used, employing mainly quantum mechanical and/or other theoretical and computational methods. Lindberg et al had shown that core electron binding energy correlate linearly to the Hammett sigma constants (σ) in substituted benzene derivatives.. Let us consider electrophilic aromatic substitution at para position of mono substituted benzene Lindberg et al had shown that core electron binding energy correlate linearly to the Hammett sigma constants (σ) in substituted benzene derivatives. Let us consider electrophilic aromatic substitution at para position of mono substituted benzene

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