Utilizing the σ-complex stability for quantifying reactivity in nucleophilic substitution of aromatic fluorides.

ABSTRACT: A computational approach using density functional theory to compute the energies of the possible σ-complex reaction intermediates, the "σ-complex approach", has been shown to be very useful in predicting regioselectivity, in electrophilic as well as nucleophilic aromatic substitution. In this article we give a short overview of the background for these investigations and the general requirements for predictive reactivity models for the pharmaceutical industry. We also present new results regarding the reaction rates and regioselectivities in nucleophilic substitution of fluorinated aromatics. They were rationalized by investigating linear correlations between experimental rate constants (k) from the literature with a theoretical quantity, which we call the sigma stability (SS). The SS is t

SUBMITTER: Liljenberg M 

PROVIDER: S-EPMC3678587 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature