Why 1,2-quinone derivatives are more stable than their 2,3-analogues?
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| 024 | 7 | 0 | |a 10.1007/s00214-015-1635-5 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00214-015-1635-5 | ||
| 245 | 0 | 0 | |a Why 1,2-quinone derivatives are more stable than their 2,3-analogues? |h [Elektronische Daten] |c [Halina Szatylowicz, Tadeusz Krygowski, Miquel Solà, Marcin Palusiak, Justyna Dominikowska, Olga Stasyuk, Jordi Poater] |
| 520 | 3 | |a 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. | |
| 540 | |a The Author(s), 2015 | ||
| 690 | 7 | |a Quinones |2 nationallicence | |
| 690 | 7 | |a Benzenoids |2 nationallicence | |
| 690 | 7 | |a Energy decomposition analysis |2 nationallicence | |
| 690 | 7 | |a Aromaticity |2 nationallicence | |
| 700 | 1 | |a Szatylowicz |D Halina |u Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland |4 aut | |
| 700 | 1 | |a Krygowski |D Tadeusz |u Department of Chemistry, Warsaw University, Pasteura 1, 02-093, Warsaw, Poland |4 aut | |
| 700 | 1 | |a Solà |D Miquel |u Departament de Química, Institut de Química Computacional i Catàlisi, Universitat de Girona, Campus de Montilivi, 17071, Girona, Catalonia, Spain |4 aut | |
| 700 | 1 | |a Palusiak |D Marcin |u Department of Theoretical and Structural Chemistry, Faculty of Chemistry, University of Łódź, Pomorska 163/165, 90-236, Lodz, Poland |4 aut | |
| 700 | 1 | |a Dominikowska |D Justyna |u Department of Theoretical and Structural Chemistry, Faculty of Chemistry, University of Łódź, Pomorska 163/165, 90-236, Lodz, Poland |4 aut | |
| 700 | 1 | |a Stasyuk |D Olga |u Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland |4 aut | |
| 700 | 1 | |a Poater |D Jordi |u Department of Theoretical Chemistry, Amsterdam Center for Multiscale Modeling, Vrije Universiteit, De Boelelaan 1083, 1081HV, Amsterdam, The Netherlands |4 aut | |
| 773 | 0 | |t Theoretical Chemistry Accounts |d Springer Berlin Heidelberg |g 134/3(2015-03-01), 1-14 |x 1432-881X |q 134:3<1 |1 2015 |2 134 |o 214 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00214-015-1635-5 |q text/html |z Onlinezugriff via DOI |
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| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
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| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00214-015-1635-5 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Szatylowicz |D Halina |u Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Krygowski |D Tadeusz |u Department of Chemistry, Warsaw University, Pasteura 1, 02-093, Warsaw, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Solà |D Miquel |u Departament de Química, Institut de Química Computacional i Catàlisi, Universitat de Girona, Campus de Montilivi, 17071, Girona, Catalonia, Spain |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Palusiak |D Marcin |u Department of Theoretical and Structural Chemistry, Faculty of Chemistry, University of Łódź, Pomorska 163/165, 90-236, Lodz, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Dominikowska |D Justyna |u Department of Theoretical and Structural Chemistry, Faculty of Chemistry, University of Łódź, Pomorska 163/165, 90-236, Lodz, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Stasyuk |D Olga |u Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Poater |D Jordi |u Department of Theoretical Chemistry, Amsterdam Center for Multiscale Modeling, Vrije Universiteit, De Boelelaan 1083, 1081HV, Amsterdam, The Netherlands |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Theoretical Chemistry Accounts |d Springer Berlin Heidelberg |g 134/3(2015-03-01), 1-14 |x 1432-881X |q 134:3<1 |1 2015 |2 134 |o 214 | ||