Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramides

We report the X-ray solid state structures of two tertiary squaramides, i.e. 3-(diethylamino)-4-ethoxy-cyclobutene-1,2-dione (1) and bis-3,4-(diethylamino)-cyclobutene-1,2-dione (2). Compound 1 forms electrostatically compressed dimers in the solid state. Moreover, compound 2 exhibits a remarkable s...

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Authors: Prohens López, Rafael, Portell Bueso, Anna, Font Bardia, Ma. Mercedes, Bauzá, Antonio, Frontera, Antonio
Format: article
Status:Published version
Publication Date:2016
Country:España
Institution:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repository:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/118854
Online Access:https://hdl.handle.net/2445/118854
Access Level:Open access
Keyword:Polimorfisme (Cristal·lografia)
Química supramolecular
Polymorphism (Crystallography)
Supramolecular chemistry
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spelling Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramidesProhens López, RafaelPortell Bueso, AnnaFont Bardia, Ma. MercedesBauzá, AntonioFrontera, AntonioPolimorfisme (Cristal·lografia)Química supramolecularPolymorphism (Crystallography)Supramolecular chemistryWe report the X-ray solid state structures of two tertiary squaramides, i.e. 3-(diethylamino)-4-ethoxy-cyclobutene-1,2-dione (1) and bis-3,4-(diethylamino)-cyclobutene-1,2-dione (2). Compound 1 forms electrostatically compressed dimers in the solid state. Moreover, compound 2 exhibits a remarkable solid state architecture resembling a lipid bilayer. This supramolecular assembly has been analyzed using high level DFT calculations and Bader's theory of "atoms-in-molecules". The antiparallel CO⋯CO interactions of the cyclobutenedione rings and hydrophobic interactions involving the ethyl chains are crucial for the formation of the bilayer assembly in the solid stateRoyal Society of Chemistry2017201720162017info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion7 p.application/pdfhttps://hdl.handle.net/2445/118854Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)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/10.1039/C6CE01299JCrystengcomm, 2016, vol. 18, p. 6437-6443https://doi.org/10.1039/C6CE01299Jcc-by (c) Prohens López, Rafael et al., 2016http://creativecommons.org/licenses/by/3.0/esinfo:eu-repo/semantics/openAccessoai:recercat.cat:2445/1188542026-05-29T05:05:01Z
dc.title.none.fl_str_mv Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramides
title Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramides
spellingShingle Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramides
Prohens López, Rafael
Polimorfisme (Cristal·lografia)
Química supramolecular
Polymorphism (Crystallography)
Supramolecular chemistry
title_short Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramides
title_full Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramides
title_fullStr Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramides
title_full_unstemmed Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramides
title_sort Experimental and theoretical study of weak intermolecular interactions in crystalline tertiary squaramides
dc.creator.none.fl_str_mv Prohens López, Rafael
Portell Bueso, Anna
Font Bardia, Ma. Mercedes
Bauzá, Antonio
Frontera, Antonio
author Prohens López, Rafael
author_facet Prohens López, Rafael
Portell Bueso, Anna
Font Bardia, Ma. Mercedes
Bauzá, Antonio
Frontera, Antonio
author_role author
author2 Portell Bueso, Anna
Font Bardia, Ma. Mercedes
Bauzá, Antonio
Frontera, Antonio
author2_role author
author
author
author
dc.subject.none.fl_str_mv Polimorfisme (Cristal·lografia)
Química supramolecular
Polymorphism (Crystallography)
Supramolecular chemistry
topic Polimorfisme (Cristal·lografia)
Química supramolecular
Polymorphism (Crystallography)
Supramolecular chemistry
description We report the X-ray solid state structures of two tertiary squaramides, i.e. 3-(diethylamino)-4-ethoxy-cyclobutene-1,2-dione (1) and bis-3,4-(diethylamino)-cyclobutene-1,2-dione (2). Compound 1 forms electrostatically compressed dimers in the solid state. Moreover, compound 2 exhibits a remarkable solid state architecture resembling a lipid bilayer. This supramolecular assembly has been analyzed using high level DFT calculations and Bader's theory of "atoms-in-molecules". The antiparallel CO⋯CO interactions of the cyclobutenedione rings and hydrophobic interactions involving the ethyl chains are crucial for the formation of the bilayer assembly in the solid state
publishDate 2016
dc.date.none.fl_str_mv 2016
2017
2017
2017
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/2445/118854
url https://hdl.handle.net/2445/118854
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/10.1039/C6CE01299J
Crystengcomm, 2016, vol. 18, p. 6437-6443
https://doi.org/10.1039/C6CE01299J
dc.rights.none.fl_str_mv cc-by (c) Prohens López, Rafael et al., 2016
http://creativecommons.org/licenses/by/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Prohens López, Rafael et al., 2016
http://creativecommons.org/licenses/by/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 7 p.
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)
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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