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Abstract
The relative extent of protonation in oxygen and carbon atoms and the position of protonation in carbons depend on several factors. We seek to locate the frontier molecular orbitals involved in the protonation reactions of substituted phenols using the FERMO concept through the MOLPROJ software, to compare the computational results with experimental NMR data obtained in the literature. We evaluate computationally the stereo-electronic effects that govern reactions of aromatic electrophilic substitution using an experimental study as an example. The MOLPROJ returned a percentage of correct answers of approximately 86% in the protonation sites. The experimental results on the protonation sites were rationalized in terms of stereoelectronic effects.
Supplementary materials
Title
SUPPLEMENTARY MATERIAL
Description
Figure S1: Shapes of the four highest MOs for structures A and B. 2
Figure S2: Shapes of the four highest MOs for the structure A replaced with fluorine atom at the position meta. 2
Figure S3: Shapes of the four highest MOs for the structure B replaced with fluorine atom at the position meta. 2
Table S-I: results for the degrees of localization (Γ) and energies of the four highest MOs for all oxygen and aromatic carbon atoms in the 01-17 phenol compounds as returned by MOLPROJ. 3
Table S-II: results for the degrees of localization (Γ) and energies of the four highest MOs for all oxygen and aromatic carbon atoms in the phenolic strucutures A and B (derived from phenol 02) and fluorinated structures A’ and B’ (derived from 3-fluorophenol) as returned by MOLPROJ. 6
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