Biological and Medicinal Chemistry

A Web Tool for Calculating Substituent Descriptors Compatible with Hammett Sigma Constants

Peter Ertl Novartis Institutes for BioMedical Research

Abstract

Electron donating or accepting power of organic substituents is an important parameter affecting many properties of parent molecules, most notably their reactivity and pKa of ionizable groups. These substituent properties are usually described by Hammett sigma constants obtained by measuring ionization of substituted benzoic acids. Although values of these constants have been measured for the most common functional groups, data for many important substituents are not available. Some time ago we reported a method to calculate substituent descriptors compatible with Hammett sigma constants using quantum chemically derived parameters. The present publication revisits the older study by applying more sophisticated methodology and a larger training data set, as well as introduces a free web tool allowing to calculate substituent descriptors compatible with Hammett sigma constants available at https://bitly.com/getsigmas.


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