Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbons

It is well-known that kinked phenacenes are more stable than their isomeric linear acenes, the archetypal example being phenanthrene that is more stable than anthracene by about 4-8 kcal/mol. In previous studies, the origin of the higher stability of kinked polycyclic aromatic hydrocarbons (PAHs) wa...

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Detalhes bibliográficos
Autores: Poater i Teixidor, Jordi, Duran, Miquel, Solà, Miquel
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/176568
Acesso em linha:https://hdl.handle.net/2445/176568
Access Level:acceso abierto
Palavra-chave:Teoria del funcional de densitat
Hidrocarburs aromàtics policíclics
Density functionals
Polycyclic aromatic hydrocarbons
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spelling Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbonsPoater i Teixidor, JordiDuran, MiquelSolà, MiquelTeoria del funcional de densitatHidrocarburs aromàtics policíclicsDensity functionalsPolycyclic aromatic hydrocarbonsIt is well-known that kinked phenacenes are more stable than their isomeric linear acenes, the archetypal example being phenanthrene that is more stable than anthracene by about 4-8 kcal/mol. In previous studies, the origin of the higher stability of kinked polycyclic aromatic hydrocarbons (PAHs) was found to be better π-bonding interactions, i.e., larger aromaticity, in kinked as compared to linear PAHs. Some years ago, however, Dominikowska and Palusiak (2011) found that dicationic linear anthracene is more stable than the dicationic kinked phenanthrene. Therefore, these authors showed that, in some cases, the linear topology in PAHs can be preferred over the kinked one. Our results using energy decomposition analyses in combination with the turn-upside-down approach show that the origin of the higher stability of dicationic anthracene is the same as in the neutral species, i.e., better π-bonding interactions. A similar result is found for the kinked and straight pyrano-chromenes. We conclude that the aromaticity is the driving force that determines the relative stability of kinked vs. straight topologies in PAHs.Frontiers Media2021202120182021info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion14 p.application/pdfhttps://hdl.handle.net/2445/176568Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésReproducció del document publicat a: https://doi.org/10.3389/fchem.2018.00561Frontiers in Chemistry, 2018, vol. 6, p. 561https://doi.org/10.3389/fchem.2018.00561cc-by (c) Poater i Teixidor, Jordi et al., 2018http://creativecommons.org/licenses/by/3.0/esinfo:eu-repo/semantics/openAccessoai:recercat.cat:2445/1765682026-05-29T05:05:01Z
dc.title.none.fl_str_mv Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbons
title Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbons
spellingShingle Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbons
Poater i Teixidor, Jordi
Teoria del funcional de densitat
Hidrocarburs aromàtics policíclics
Density functionals
Polycyclic aromatic hydrocarbons
title_short Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbons
title_full Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbons
title_fullStr Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbons
title_full_unstemmed Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbons
title_sort Aromaticity determines the relative stability of kinked vs. straight topologies in polycyclic aromatic hydrocarbons
dc.creator.none.fl_str_mv Poater i Teixidor, Jordi
Duran, Miquel
Solà, Miquel
author Poater i Teixidor, Jordi
author_facet Poater i Teixidor, Jordi
Duran, Miquel
Solà, Miquel
author_role author
author2 Duran, Miquel
Solà, Miquel
author2_role author
author
dc.subject.none.fl_str_mv Teoria del funcional de densitat
Hidrocarburs aromàtics policíclics
Density functionals
Polycyclic aromatic hydrocarbons
topic Teoria del funcional de densitat
Hidrocarburs aromàtics policíclics
Density functionals
Polycyclic aromatic hydrocarbons
description It is well-known that kinked phenacenes are more stable than their isomeric linear acenes, the archetypal example being phenanthrene that is more stable than anthracene by about 4-8 kcal/mol. In previous studies, the origin of the higher stability of kinked polycyclic aromatic hydrocarbons (PAHs) was found to be better π-bonding interactions, i.e., larger aromaticity, in kinked as compared to linear PAHs. Some years ago, however, Dominikowska and Palusiak (2011) found that dicationic linear anthracene is more stable than the dicationic kinked phenanthrene. Therefore, these authors showed that, in some cases, the linear topology in PAHs can be preferred over the kinked one. Our results using energy decomposition analyses in combination with the turn-upside-down approach show that the origin of the higher stability of dicationic anthracene is the same as in the neutral species, i.e., better π-bonding interactions. A similar result is found for the kinked and straight pyrano-chromenes. We conclude that the aromaticity is the driving force that determines the relative stability of kinked vs. straight topologies in PAHs.
publishDate 2018
dc.date.none.fl_str_mv 2018
2021
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/176568
url https://hdl.handle.net/2445/176568
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.3389/fchem.2018.00561
Frontiers in Chemistry, 2018, vol. 6, p. 561
https://doi.org/10.3389/fchem.2018.00561
dc.rights.none.fl_str_mv cc-by (c) Poater i Teixidor, Jordi et al., 2018
http://creativecommons.org/licenses/by/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Poater i Teixidor, Jordi et al., 2018
http://creativecommons.org/licenses/by/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 14 p.
application/pdf
dc.publisher.none.fl_str_mv Frontiers Media
publisher.none.fl_str_mv Frontiers Media
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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