Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density Analysis

<p> In an effort to better understand the nature of noncovalent carbon-bonding interactions, we undertook accurate high-resolution X-ray diffraction analysis of single crystals of 1,1,2,2-tetracyanocyclopropane. We selected this compound to study the fundamental characteristics of carbon-bondi...

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Autores: Escudero-Adán, Eduardo C., Bauza, Antonio, Frontera, Antonio, Ballester,Pablo
Tipo de documento: artigo
Data de publicação:2015
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositório:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/305815
Acesso em linha:http://hdl.handle.net/2072/305815
https://doi.org/10.1002/cphc.201500437
Access Level:Acceso aberto
Palavra-chave:ab initio calculations
charge density
noncovalent carbon bonding
supramolecular chemistry
sigma-hole interactions
chalcogen-chalcogen
interactions
sigma-hole
small-molecule
halogen bonds
hydrogen
tetrel
derivatives
refinement
complexes
quality
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spelling Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density AnalysisEscudero-Adán, Eduardo C.Bauza, AntonioFrontera, AntonioBallester,Pabloab initio calculationscharge densitynoncovalent carbon bondingsupramolecular chemistrysigma-hole interactionschalcogen-chalcogeninteractionssigma-holesmall-moleculehalogen bondshydrogentetrelderivativesrefinementcomplexesquality<p> In an effort to better understand the nature of noncovalent carbon-bonding interactions, we undertook accurate high-resolution X-ray diffraction analysis of single crystals of 1,1,2,2-tetracyanocyclopropane. We selected this compound to study the fundamental characteristics of carbon-bonding interactions, because it provides accessible sigma holes. The study required extremely accurate experimental diffraction data, because the interaction of interest is weak. The electron-density distribution around the carbon nuclei, as shown by the experimental maps of the electrophilic bowl defined by a (CN)(2)CC(CN)(2) unit, was assigned as the origin of the interaction. This fact was also evidenced by plotting the (2)(r) distribution. Taken together, the obtained results clearly indicate that noncovalent carbon bonding can be explained as an interaction between confronted oppositely polarized regions. The interaction is, thus electrophilic-nucleophilic (electrostatic) in nature and unambiguously considered as attractive.</p> <p> &nbsp;</p>WILEY-V C H VERLAG GMBH2015info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/2072/305815https://doi.org/10.1002/cphc.201500437RECERCAT (Dipòsit de la Recerca de Catalunya)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésMINECO with FEDER fundsSevero Ochoa Excellence Accreditation 2014– 2018Programa Estatal de I+D+i Orientada a los Retos de la SociedadSENSOSALUDChemphyschemSEV-2013–0319CTQ2014– 56295-R© 2015 Wiley-VCH Verlag GmbH & Co. KGaAinfo:eu-repo/semantics/openAccessoai:recercat.cat:2072/3058152026-05-29T05:05:01Z
dc.title.none.fl_str_mv Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density Analysis
title Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density Analysis
spellingShingle Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density Analysis
Escudero-Adán, Eduardo C.
ab initio calculations
charge density
noncovalent carbon bonding
supramolecular chemistry
sigma-hole interactions
chalcogen-chalcogen
interactions
sigma-hole
small-molecule
halogen bonds
hydrogen
tetrel
derivatives
refinement
complexes
quality
title_short Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density Analysis
title_full Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density Analysis
title_fullStr Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density Analysis
title_full_unstemmed Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density Analysis
title_sort Nature of Noncovalent Carbon-Bonding Interactions Derived from Experimental Charge-Density Analysis
dc.creator.none.fl_str_mv Escudero-Adán, Eduardo C.
Bauza, Antonio
Frontera, Antonio
Ballester,Pablo
author Escudero-Adán, Eduardo C.
author_facet Escudero-Adán, Eduardo C.
Bauza, Antonio
Frontera, Antonio
Ballester,Pablo
author_role author
author2 Bauza, Antonio
Frontera, Antonio
Ballester,Pablo
author2_role author
author
author
dc.subject.none.fl_str_mv ab initio calculations
charge density
noncovalent carbon bonding
supramolecular chemistry
sigma-hole interactions
chalcogen-chalcogen
interactions
sigma-hole
small-molecule
halogen bonds
hydrogen
tetrel
derivatives
refinement
complexes
quality
topic ab initio calculations
charge density
noncovalent carbon bonding
supramolecular chemistry
sigma-hole interactions
chalcogen-chalcogen
interactions
sigma-hole
small-molecule
halogen bonds
hydrogen
tetrel
derivatives
refinement
complexes
quality
description <p> In an effort to better understand the nature of noncovalent carbon-bonding interactions, we undertook accurate high-resolution X-ray diffraction analysis of single crystals of 1,1,2,2-tetracyanocyclopropane. We selected this compound to study the fundamental characteristics of carbon-bonding interactions, because it provides accessible sigma holes. The study required extremely accurate experimental diffraction data, because the interaction of interest is weak. The electron-density distribution around the carbon nuclei, as shown by the experimental maps of the electrophilic bowl defined by a (CN)(2)CC(CN)(2) unit, was assigned as the origin of the interaction. This fact was also evidenced by plotting the (2)(r) distribution. Taken together, the obtained results clearly indicate that noncovalent carbon bonding can be explained as an interaction between confronted oppositely polarized regions. The interaction is, thus electrophilic-nucleophilic (electrostatic) in nature and unambiguously considered as attractive.</p> <p> &nbsp;</p>
publishDate 2015
dc.date.none.fl_str_mv 2015
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/305815
https://doi.org/10.1002/cphc.201500437
url http://hdl.handle.net/2072/305815
https://doi.org/10.1002/cphc.201500437
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv MINECO with FEDER funds
Severo Ochoa Excellence Accreditation 2014– 2018
Programa Estatal de I+D+i Orientada a los Retos de la Sociedad
SENSOSALUD
Chemphyschem
SEV-2013–0319
CTQ2014– 56295-R
dc.rights.none.fl_str_mv © 2015 Wiley-VCH Verlag GmbH & Co. KGaA
info:eu-repo/semantics/openAccess
rights_invalid_str_mv © 2015 Wiley-VCH Verlag GmbH & Co. KGaA
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv WILEY-V C H VERLAG GMBH
publisher.none.fl_str_mv WILEY-V C H VERLAG GMBH
dc.source.none.fl_str_mv RECERCAT (Dipòsit de la Recerca de Catalunya)
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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score 15,812429

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