Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromo

Autores
Echeverría, Gustavo Alberto; Fantoni, Adolfo Carlos; Marañón, Julio; Punte, Graciela María del Carmen
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Molecular geometry, crystal packing and thermal stability of trans-1,4-cyclohexanedicarboxylic acid, 1,4-dibromo (I) are examined, in order to analyse the relative influence of the different intermolecular interactions at play. From a comparison with the corresponding properties of trans1,4-cyclohexanedicarboxylic acid (II), some insights on the results of the competition between Br and carboxylic groups are obtained. In the crystalline state, the molecules of both compounds present chair centrosymmetric geometry and build infinite chains through ring hydrogen bonds involving the carboxylic groups. These groups are axial in I and equatorial in II, giving rise to different assembly of the chains. In both compounds there is in general good agreement between the in-crystal geometry and the B3LYP/LanL2DZ optimized geometry of the corresponding isolated molecule. The only significant differences are related to the carboxylic groups. The intermolecular contacts in I have been rationalized on the basis of a graph set analysis. A molecular dynamics based method has been used to analyse the temperature dependence of the mean life time of the different kinds of hydrogen bonds characterized in I. It has been found that the O–H⋅ ⋅O and C–H⋅ ⋅O(carbonyl) interactions are the main source of thermal stability. The melting point of I determined within this approach agrees very well with the experimental value.
Instituto de Física La Plata
Facultad de Ingeniería
Materia
Física
Ingeniería
Crystal packing
molecular dynamics
thermal stability
hydrogen bond
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/138822

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repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromoEcheverría, Gustavo AlbertoFantoni, Adolfo CarlosMarañón, JulioPunte, Graciela María del CarmenFísicaIngenieríaCrystal packingmolecular dynamicsthermal stabilityhydrogen bondMolecular geometry, crystal packing and thermal stability of trans-1,4-cyclohexanedicarboxylic acid, 1,4-dibromo (I) are examined, in order to analyse the relative influence of the different intermolecular interactions at play. From a comparison with the corresponding properties of trans1,4-cyclohexanedicarboxylic acid (II), some insights on the results of the competition between Br and carboxylic groups are obtained. In the crystalline state, the molecules of both compounds present chair centrosymmetric geometry and build infinite chains through ring hydrogen bonds involving the carboxylic groups. These groups are axial in I and equatorial in II, giving rise to different assembly of the chains. In both compounds there is in general good agreement between the in-crystal geometry and the B3LYP/LanL2DZ optimized geometry of the corresponding isolated molecule. The only significant differences are related to the carboxylic groups. The intermolecular contacts in I have been rationalized on the basis of a graph set analysis. A molecular dynamics based method has been used to analyse the temperature dependence of the mean life time of the different kinds of hydrogen bonds characterized in I. It has been found that the O–H⋅ ⋅O and C–H⋅ ⋅O(carbonyl) interactions are the main source of thermal stability. The melting point of I determined within this approach agrees very well with the experimental value.Instituto de Física La PlataFacultad de Ingeniería2005-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf571-579http://sedici.unlp.edu.ar/handle/10915/138822enginfo:eu-repo/semantics/altIdentifier/issn/1040-0400info:eu-repo/semantics/altIdentifier/issn/1572-9001info:eu-repo/semantics/altIdentifier/doi/10.1007/s11224-005-6097-2info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:31:52Zoai:sedici.unlp.edu.ar:10915/138822Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:31:52.438SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromo
title Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromo
spellingShingle Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromo
Echeverría, Gustavo Alberto
Física
Ingeniería
Crystal packing
molecular dynamics
thermal stability
hydrogen bond
title_short Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromo
title_full Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromo
title_fullStr Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromo
title_full_unstemmed Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromo
title_sort Non-Bonded Intermolecular Interactions and Crystal Stability of trans -1,4-Cyclohexanedicarboxylic Acid, 1,4-dibromo
dc.creator.none.fl_str_mv Echeverría, Gustavo Alberto
Fantoni, Adolfo Carlos
Marañón, Julio
Punte, Graciela María del Carmen
author Echeverría, Gustavo Alberto
author_facet Echeverría, Gustavo Alberto
Fantoni, Adolfo Carlos
Marañón, Julio
Punte, Graciela María del Carmen
author_role author
author2 Fantoni, Adolfo Carlos
Marañón, Julio
Punte, Graciela María del Carmen
author2_role author
author
author
dc.subject.none.fl_str_mv Física
Ingeniería
Crystal packing
molecular dynamics
thermal stability
hydrogen bond
topic Física
Ingeniería
Crystal packing
molecular dynamics
thermal stability
hydrogen bond
dc.description.none.fl_txt_mv Molecular geometry, crystal packing and thermal stability of trans-1,4-cyclohexanedicarboxylic acid, 1,4-dibromo (I) are examined, in order to analyse the relative influence of the different intermolecular interactions at play. From a comparison with the corresponding properties of trans1,4-cyclohexanedicarboxylic acid (II), some insights on the results of the competition between Br and carboxylic groups are obtained. In the crystalline state, the molecules of both compounds present chair centrosymmetric geometry and build infinite chains through ring hydrogen bonds involving the carboxylic groups. These groups are axial in I and equatorial in II, giving rise to different assembly of the chains. In both compounds there is in general good agreement between the in-crystal geometry and the B3LYP/LanL2DZ optimized geometry of the corresponding isolated molecule. The only significant differences are related to the carboxylic groups. The intermolecular contacts in I have been rationalized on the basis of a graph set analysis. A molecular dynamics based method has been used to analyse the temperature dependence of the mean life time of the different kinds of hydrogen bonds characterized in I. It has been found that the O–H⋅ ⋅O and C–H⋅ ⋅O(carbonyl) interactions are the main source of thermal stability. The melting point of I determined within this approach agrees very well with the experimental value.
Instituto de Física La Plata
Facultad de Ingeniería
description Molecular geometry, crystal packing and thermal stability of trans-1,4-cyclohexanedicarboxylic acid, 1,4-dibromo (I) are examined, in order to analyse the relative influence of the different intermolecular interactions at play. From a comparison with the corresponding properties of trans1,4-cyclohexanedicarboxylic acid (II), some insights on the results of the competition between Br and carboxylic groups are obtained. In the crystalline state, the molecules of both compounds present chair centrosymmetric geometry and build infinite chains through ring hydrogen bonds involving the carboxylic groups. These groups are axial in I and equatorial in II, giving rise to different assembly of the chains. In both compounds there is in general good agreement between the in-crystal geometry and the B3LYP/LanL2DZ optimized geometry of the corresponding isolated molecule. The only significant differences are related to the carboxylic groups. The intermolecular contacts in I have been rationalized on the basis of a graph set analysis. A molecular dynamics based method has been used to analyse the temperature dependence of the mean life time of the different kinds of hydrogen bonds characterized in I. It has been found that the O–H⋅ ⋅O and C–H⋅ ⋅O(carbonyl) interactions are the main source of thermal stability. The melting point of I determined within this approach agrees very well with the experimental value.
publishDate 2005
dc.date.none.fl_str_mv 2005-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
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info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/138822
url http://sedici.unlp.edu.ar/handle/10915/138822
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1040-0400
info:eu-repo/semantics/altIdentifier/issn/1572-9001
info:eu-repo/semantics/altIdentifier/doi/10.1007/s11224-005-6097-2
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
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