Intramolecular halogen-halogen bonds?

By analysing the properties of the electron density in the structurally simple perhalogenated ethanes, X3C-CY3 (X, Y = F, Cl), a previously overlooked non-covalent attraction between halogens attached to opposite carbon atoms is found. Quantum chemical calculations extrapolated towards the full solu...

Descripción completa

Detalles Bibliográficos
Autores: Johansson, Mikael P., Swart, Marcel
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2013
País:España
Institución: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:10256/11461
Acceso en línea:http://hdl.handle.net/10256/11461
Access Level:acceso abierto
Palabra clave:Enllaços químics
Chemical bonds
Halògens
Halogens
Química quàntica
Quantum chemistry
id ES_7933d3d89ac170e4e35d60d4da4d8062
oai_identifier_str oai:recercat.cat:10256/11461
network_acronym_str ES
network_name_str España
repository_id_str
spelling Intramolecular halogen-halogen bonds?Johansson, Mikael P.Swart, MarcelEnllaços químicsChemical bondsHalògensHalogensQuímica quànticaQuantum chemistryBy analysing the properties of the electron density in the structurally simple perhalogenated ethanes, X3C-CY3 (X, Y = F, Cl), a previously overlooked non-covalent attraction between halogens attached to opposite carbon atoms is found. Quantum chemical calculations extrapolated towards the full solution of the Schrödinger equation reveal the complex nature of the interaction. When at least one of the halogens is a chlorine, the strength of the interaction is comparable to that of hydrogen bonds. Further analysis shows that the bond character is quite different from standard non-covalent halogen bonds and hydrogen bonds; no bond critical points are found between the halogens, and the σ-holes of the halogens are not utilised for bonding. Thus, the nature of the intramolecular halogen⋯halogen bonding studied here appears to be of an unusually strong van der Waals typeWe are grateful to Dr Eduard Matito, Dr Pedro Salvador, and Dr Raphael Berger for enlightening discussions. CSC - the Finnish IT Centre for Science hosted part of the calculations. This work has been supported by the Ministerio de Ciencia e Innovacion (MICINN projects JCI-2009-05953, CTQ2011-25086/BQU), the Academy of Finland (project 136079), MICINN and the European Fund for Regional Development (FEDER grant UNGI08-4E-003), and the DIUE of the Generalitat de Catalunya (project 2009SGR528)Royal Society of Chemistry (RSC)Ministerio de Ciencia e Innovación (Espanya)Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca2013info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10256/11461http://hdl.handle.net/10256/11461© Physical Chemistry Chemical Physics, 2013, vol. 15, núm. 27, p. 11543-11553Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1039/c3cp50962ainfo:eu-repo/semantics/altIdentifier/issn/1463-9076info:eu-repo/semantics/altIdentifier/eissn/1463-9084info:eu-repo/grantAgreement/MICINN//CTQ2011-25086AGAUR/2009-2014/2009 SGR-528Attribution 3.0 Spainhttp://creativecommons.org/licenses/by/3.0/es/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/114612026-05-29T05:05:01Z
dc.title.none.fl_str_mv Intramolecular halogen-halogen bonds?
title Intramolecular halogen-halogen bonds?
spellingShingle Intramolecular halogen-halogen bonds?
Johansson, Mikael P.
Enllaços químics
Chemical bonds
Halògens
Halogens
Química quàntica
Quantum chemistry
title_short Intramolecular halogen-halogen bonds?
title_full Intramolecular halogen-halogen bonds?
title_fullStr Intramolecular halogen-halogen bonds?
title_full_unstemmed Intramolecular halogen-halogen bonds?
title_sort Intramolecular halogen-halogen bonds?
dc.creator.none.fl_str_mv Johansson, Mikael P.
Swart, Marcel
author Johansson, Mikael P.
author_facet Johansson, Mikael P.
Swart, Marcel
author_role author
author2 Swart, Marcel
author2_role author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (Espanya)
Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca
dc.subject.none.fl_str_mv Enllaços químics
Chemical bonds
Halògens
Halogens
Química quàntica
Quantum chemistry
topic Enllaços químics
Chemical bonds
Halògens
Halogens
Química quàntica
Quantum chemistry
description By analysing the properties of the electron density in the structurally simple perhalogenated ethanes, X3C-CY3 (X, Y = F, Cl), a previously overlooked non-covalent attraction between halogens attached to opposite carbon atoms is found. Quantum chemical calculations extrapolated towards the full solution of the Schrödinger equation reveal the complex nature of the interaction. When at least one of the halogens is a chlorine, the strength of the interaction is comparable to that of hydrogen bonds. Further analysis shows that the bond character is quite different from standard non-covalent halogen bonds and hydrogen bonds; no bond critical points are found between the halogens, and the σ-holes of the halogens are not utilised for bonding. Thus, the nature of the intramolecular halogen⋯halogen bonding studied here appears to be of an unusually strong van der Waals type
publishDate 2013
dc.date.none.fl_str_mv 2013
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 http://hdl.handle.net/10256/11461
http://hdl.handle.net/10256/11461
url http://hdl.handle.net/10256/11461
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c3cp50962a
info:eu-repo/semantics/altIdentifier/issn/1463-9076
info:eu-repo/semantics/altIdentifier/eissn/1463-9084
info:eu-repo/grantAgreement/MICINN//CTQ2011-25086
AGAUR/2009-2014/2009 SGR-528
dc.rights.none.fl_str_mv Attribution 3.0 Spain
http://creativecommons.org/licenses/by/3.0/es/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution 3.0 Spain
http://creativecommons.org/licenses/by/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry (RSC)
publisher.none.fl_str_mv Royal Society of Chemistry (RSC)
dc.source.none.fl_str_mv © Physical Chemistry Chemical Physics, 2013, vol. 15, núm. 27, p. 11543-11553
Articles publicats (D-Q)
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
_version_ 1869411330641887232
score 15.81155

Similares en LA Referencia