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
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/138822
Ver los metadatos del registro completo
id |
SEDICI_0e862c6ecfce8141d4a6660eea0e2406 |
---|---|
oai_identifier_str |
oai:sedici.unlp.edu.ar:10915/138822 |
network_acronym_str |
SEDICI |
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 Articulo http://purl.org/coar/resource_type/c_6501 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) |
dc.format.none.fl_str_mv |
application/pdf 571-579 |
dc.source.none.fl_str_mv |
reponame:SEDICI (UNLP) instname:Universidad Nacional de La Plata instacron:UNLP |
reponame_str |
SEDICI (UNLP) |
collection |
SEDICI (UNLP) |
instname_str |
Universidad Nacional de La Plata |
instacron_str |
UNLP |
institution |
UNLP |
repository.name.fl_str_mv |
SEDICI (UNLP) - Universidad Nacional de La Plata |
repository.mail.fl_str_mv |
alira@sedici.unlp.edu.ar |
_version_ |
1844616198314000384 |
score |
13.070432 |