Opis

• Tytuł:
  Why 1,2‑quinone derivatives are more stable than their 2,3‑analogues?
• Twórca:
  Szatylowicz, Halina;
  Krygowski, Tadeusz M.;
  Solà, Miquel;
  Palusiak, Marcin;
  Dominikowska, Justyna;
  Stasyuk, Olga A.;
  Poater, Jordi
• Współtwórca:
  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
• Opis:
  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.
• Dostępność obiektu:
  Dostęp otwarty
• Prawa:
  Uznanie autorstwa 3.0 Polska;
  http://creativecommons.org/licenses/by/3.0/pl
• Data:
  2015.05.11;
  2015.02.25
• Typ:
  Article
• Język:
  angielski
• Format:
  application/pdf
• Wydawca:
  Springer Berlin Heidelberg
• Relacja:
  Theoretical Chemistry Accounts;134:35
• Temat i słowa kluczowe:
  Quinones;
  Benzenoids;
  Energy decomposition analysis;
  Aromaticity
• Identyfikator:
  1432-2234;
  http://hdl.handle.net/11089/8710
• Dostawca danych:
  Repozytorium Uniwersytetu Łódzkiego
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