Object's details: Why 1,2‑quinone derivatives are more stable than their 2,3‑analogues?

Provider:Repozytorium Uniwersytetu Łódzkiego

Description

Title:
Why 1,2‑quinone derivatives are more stable than their 2,3‑analogues?
Creator:
Szatylowicz, Halina;
Krygowski, Tadeusz M.;
Solà, Miquel;
Palusiak, Marcin;
Dominikowska, Justyna;
Stasyuk, Olga A.;
Poater, Jordi
Contributor:
Szatylowicz Halina, Warsaw University of Technology Faculty of Chemistry;
Krygowski Tadeusz M., Warsaw University Department of Chemistry;
Solà Miquel, Universitat de Girona, Departament de Química, Institut de Química Computacional i Catàlisi;
Palusiak Marcin, University of Łódź, Department of Theoretical and Structural Chemistry, Faculty of Chemistry;
Dominikowska Justyna, University of Łódź, Department of Theoretical and Structural Chemistry, Faculty of Chemistry;
Stasyuk Olga A., Warsaw University of Technology Faculty of Chemistry;
Poater Jordi, Vrije Universiteit, Department of Theoretical Chemistry, Amsterdam Center for Multiscale Modeling;
halina@ch.pw.edu.pl
Description:
In this work, we have studied the relative stability of 1,2- and 2,3-quinones. While 1,2-quinones have a closed-shell singlet ground state, the ground state for the studied 2,3-isomers is open-shell singlet, except for 2,3-naphthaquinone that has a closed-shell singlet ground state. In all cases, 1,2-quinones are more stable than their 2,3-counterparts. We analyzed the reasons for the higher stability of the 1,2-isomers through energy decomposition analysis in the framework of Kohn–Sham molecular orbital theory. The results showed that we have to trace the origin of 1,2-quinones’ enhanced stability to the more efficient bonding in the π-electron system due to more favorable overlap between the SOMOπ of the ·C4n−2H2n–CH·· and ··CH–CO–CO· fragments in the 1,2-arrangement. Furthermore, whereas 1,2-quinones present a constant trend with their elongation for all analyzed properties (geometric, energetic, and electronic), 2,3-quinone derivatives present a substantial breaking in monotonicity.;
European Union in the framework of European Social Fund through the Warsaw University of Technology Development Programme. O.A. S., H. S. and T.M. K.
Object availability:
free access
Rights:
Uznanie autorstwa 3.0 Polska;
http://creativecommons.org/licenses/by/3.0/pl
Date:
2015.05.11;
2015.02.25
Type:
Article
Language:
English
Format:
application/pdf
Publisher:
Springer Berlin Heidelberg
Relation:
Theoretical Chemistry Accounts;134:35
Subject:
Quinones;
Benzenoids;
Energy decomposition analysis;
Aromaticity
Identifier:
1432-2234;
http://hdl.handle.net/11089/8710
Data provider:
Repozytorium Uniwersytetu Łódzkiego

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Object's details: Why 1,2‑quinone derivatives are more stable than their 2,3‑analogues?

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