Understanding the nature of bonding interactions in the carbonic acid dimers
Carbonic acid dimer, (CA)2, (H2CO3)2, helps to explain the existence of this acid as a stable species, different to a simple sum between carbon dioxide and water. Five distinct, well characterized types of intermolecular interactions contribute to the stabilization of the dimers, namely, C=O⋯H–O, H–...
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ftconicet:oai:ri.conicet.gov.ar:11336/105816 2023-10-09T21:50:40+02:00 Understanding the nature of bonding interactions in the carbonic acid dimers Zapata Escobar, Andy Danian Murillo López, Juliana Andrea Hadad, C. Z. Restrepo Cossio, Albeiro Alonso application/pdf http://hdl.handle.net/11336/105816 eng eng Springer info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007/s00894-018-3907-1 info:eu-repo/semantics/altIdentifier/doi/10.1007/s00894-018-3907-1 http://hdl.handle.net/11336/105816 Zapata Escobar, Andy Danian; Murillo López, Juliana Andrea; Hadad, C. Z.; Restrepo Cossio, Albeiro Alonso; Understanding the nature of bonding interactions in the carbonic acid dimers; Springer; Journal of Molecular Modeling; 25; 20; 1-2019; 1-10 1610-2940 0948-5023 CONICET Digital CONICET info:eu-repo/semantics/restrictedAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ BIFURCATED BONDS CARBONIC ACID HYDROGEN BONDS NBOS QTAIM https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion ftconicet https://doi.org/10.1007/s00894-018-3907-1 2023-09-24T18:36:42Z Carbonic acid dimer, (CA)2, (H2CO3)2, helps to explain the existence of this acid as a stable species, different to a simple sum between carbon dioxide and water. Five distinct, well characterized types of intermolecular interactions contribute to the stabilization of the dimers, namely, C=O⋯H–O, H–O⋯H–O, C=O⋯C=O, C=O⋯O–H, and C–O⋯O–H. In many cases, the stabilizing hydrogen bonds are of at least the same strength as in the water dimer. We dissect the nature of intermolecular interactions and assess their influence on stability. For a set of 40 (H2CO3)2 isomers, C=O⋯H–O hydrogen bonds between the carbonyl oxygen in one CA molecule and the acidic hydrogen in the hydroxyl group at a second CA molecule are the major stabilizing factors because they exhibit the shortest interaction distances, the largest orbital interaction energies, and the largest accumulation of electron densities around the corresponding bond critical points. In most cases, these are closed-shell hydrogen bonds, however, in a few instances, some covalent character is induced. Bifurcated hydrogen bonds are a common occurrence in the dimers of carbonic acid, resulting in a complex picture with multiple orbital interactions of various strengths. Two anti–anti monomers interacting via the strongest C=O⋯H–O hydrogen bonds are the ingredients for the formation of the lowest energy dimers. Fil: Zapata Escobar, Andy Danian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Modelado e Innovación Tecnológica. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Modelado e Innovación Tecnológica; Argentina. Universidad de Antioquia; Colombia Fil: Murillo López, Juliana Andrea. Universidad Andrés Bello; Chile Fil: Hadad, C. Z. Universidad de Antioquia; Colombia Fil: Restrepo Cossio, Albeiro Alonso. Universidad de Antioquia; Colombia Article in Journal/Newspaper Carbonic acid CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) Argentina Nordeste ENVELOPE(-66.867,-66.867,-68.167,-68.167) Bello ENVELOPE(-56.933,-56.933,-64.333,-64.333) Escobar ENVELOPE(-45.150,-45.150,-60.683,-60.683) Cossio ENVELOPE(-58.450,-58.450,-62.217,-62.217) Journal of Molecular Modeling 25 1 |
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Open Polar |
collection |
CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) |
op_collection_id |
ftconicet |
language |
English |
topic |
BIFURCATED BONDS CARBONIC ACID HYDROGEN BONDS NBOS QTAIM https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
spellingShingle |
BIFURCATED BONDS CARBONIC ACID HYDROGEN BONDS NBOS QTAIM https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 Zapata Escobar, Andy Danian Murillo López, Juliana Andrea Hadad, C. Z. Restrepo Cossio, Albeiro Alonso Understanding the nature of bonding interactions in the carbonic acid dimers |
topic_facet |
BIFURCATED BONDS CARBONIC ACID HYDROGEN BONDS NBOS QTAIM https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
description |
Carbonic acid dimer, (CA)2, (H2CO3)2, helps to explain the existence of this acid as a stable species, different to a simple sum between carbon dioxide and water. Five distinct, well characterized types of intermolecular interactions contribute to the stabilization of the dimers, namely, C=O⋯H–O, H–O⋯H–O, C=O⋯C=O, C=O⋯O–H, and C–O⋯O–H. In many cases, the stabilizing hydrogen bonds are of at least the same strength as in the water dimer. We dissect the nature of intermolecular interactions and assess their influence on stability. For a set of 40 (H2CO3)2 isomers, C=O⋯H–O hydrogen bonds between the carbonyl oxygen in one CA molecule and the acidic hydrogen in the hydroxyl group at a second CA molecule are the major stabilizing factors because they exhibit the shortest interaction distances, the largest orbital interaction energies, and the largest accumulation of electron densities around the corresponding bond critical points. In most cases, these are closed-shell hydrogen bonds, however, in a few instances, some covalent character is induced. Bifurcated hydrogen bonds are a common occurrence in the dimers of carbonic acid, resulting in a complex picture with multiple orbital interactions of various strengths. Two anti–anti monomers interacting via the strongest C=O⋯H–O hydrogen bonds are the ingredients for the formation of the lowest energy dimers. Fil: Zapata Escobar, Andy Danian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Modelado e Innovación Tecnológica. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Modelado e Innovación Tecnológica; Argentina. Universidad de Antioquia; Colombia Fil: Murillo López, Juliana Andrea. Universidad Andrés Bello; Chile Fil: Hadad, C. Z. Universidad de Antioquia; Colombia Fil: Restrepo Cossio, Albeiro Alonso. Universidad de Antioquia; Colombia |
format |
Article in Journal/Newspaper |
author |
Zapata Escobar, Andy Danian Murillo López, Juliana Andrea Hadad, C. Z. Restrepo Cossio, Albeiro Alonso |
author_facet |
Zapata Escobar, Andy Danian Murillo López, Juliana Andrea Hadad, C. Z. Restrepo Cossio, Albeiro Alonso |
author_sort |
Zapata Escobar, Andy Danian |
title |
Understanding the nature of bonding interactions in the carbonic acid dimers |
title_short |
Understanding the nature of bonding interactions in the carbonic acid dimers |
title_full |
Understanding the nature of bonding interactions in the carbonic acid dimers |
title_fullStr |
Understanding the nature of bonding interactions in the carbonic acid dimers |
title_full_unstemmed |
Understanding the nature of bonding interactions in the carbonic acid dimers |
title_sort |
understanding the nature of bonding interactions in the carbonic acid dimers |
publisher |
Springer |
url |
http://hdl.handle.net/11336/105816 |
long_lat |
ENVELOPE(-66.867,-66.867,-68.167,-68.167) ENVELOPE(-56.933,-56.933,-64.333,-64.333) ENVELOPE(-45.150,-45.150,-60.683,-60.683) ENVELOPE(-58.450,-58.450,-62.217,-62.217) |
geographic |
Argentina Nordeste Bello Escobar Cossio |
geographic_facet |
Argentina Nordeste Bello Escobar Cossio |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_relation |
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007/s00894-018-3907-1 info:eu-repo/semantics/altIdentifier/doi/10.1007/s00894-018-3907-1 http://hdl.handle.net/11336/105816 Zapata Escobar, Andy Danian; Murillo López, Juliana Andrea; Hadad, C. Z.; Restrepo Cossio, Albeiro Alonso; Understanding the nature of bonding interactions in the carbonic acid dimers; Springer; Journal of Molecular Modeling; 25; 20; 1-2019; 1-10 1610-2940 0948-5023 CONICET Digital CONICET |
op_rights |
info:eu-repo/semantics/restrictedAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
op_doi |
https://doi.org/10.1007/s00894-018-3907-1 |
container_title |
Journal of Molecular Modeling |
container_volume |
25 |
container_issue |
1 |
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1779313743934521344 |