Rationalising the regioselectivity of substituted phenols from the FERMO concept: stereoelectronic effects on protonation and functionalization

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F22%3A50019013" target="_blank" >RIV/62690094:18470/22:50019013 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.tandfonline.com/doi/full/10.1080/08927022.2022.2039390" target="_blank" >https://www.tandfonline.com/doi/full/10.1080/08927022.2022.2039390</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1080/08927022.2022.2039390" target="_blank" >10.1080/08927022.2022.2039390</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Rationalising the regioselectivity of substituted phenols from the FERMO concept: stereoelectronic effects on protonation and functionalization

Popis výsledku v původním jazyce

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 rationalised in terms of stereoelectronic effects. © 2022 Informa UK Limited, trading as Taylor &amp; Francis Group.

Název v anglickém jazyce

Rationalising the regioselectivity of substituted phenols from the FERMO concept: stereoelectronic effects on protonation and functionalization

Popis výsledku anglicky

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 rationalised in terms of stereoelectronic effects. © 2022 Informa UK Limited, trading as Taylor &amp; Francis Group.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2022

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Molecular simulation

ISSN

0892-7022

e-ISSN

1029-0435

Svazek periodika

48

Číslo periodika v rámci svazku

7

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

610-620

Kód UT WoS článku

000757758400001

EID výsledku v databázi Scopus

2-s2.0-85124744268