Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
- Autores
- Granifo, Juan; Arévalo, Beatriz; Gaviño, Rubén; Suarez, Sebastian; Baggio, Ricardo Fortunato
- Año de publicación
- 2016
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- 4′-Substituted derivatives of 2,2′:6′,2′′-terpyridine with N-containing heteroaromatic substituents, such as pyridyl groups, might be able to coordinate metal centres through the extra N-donor atom, in addition to the chelating terpyridine N atoms. The incorporation of these peripheral N-donor sites would also allow for the diversification of the types of noncovalent interactions present, such as hydrogen bonding and π-π stacking. The title compound, C24H16N4, consists of a 2,2′:6′,2′′-terpyridine nucleus (tpy), with a pendant isoquinoline group (isq) bound at the central pyridine (py) ring. The tpy nucleus deviates slightly from planarity, with interplanar angles between the lateral and central py rings in the range 2.24(7)-7.90(7)°, while the isq group is rotated significantly [by 46.57(6)°] out of this planar scheme, associated with a short Htpy⋯Hisq contact of 2.32Å. There are no strong noncovalent interactions in the structure, the main ones being of the π-π and C - H⋯π types, giving rise to columnar arrays along [001], further linked by C - H⋯N hydrogen bonds into a three-dimensional supramolecular structure. An Atoms In Molecules (AIM) analysis of the noncovalent interactions provided illuminating results, and while confirming the bonding character for all those interactions unquestionable from a geometrical point of view, it also provided answers for some cases where geometric parameters are not informative, in particular, the short Htpy⋯Hisq contact of 2.32Å to which AIM ascribed an attractive character.
Fil: Granifo, Juan. Universidad de La Frontera; Chile
Fil: Arévalo, Beatriz. Universidad de La Frontera; Chile
Fil: Gaviño, Rubén. Universidad Nacional Autónoma de México; México
Fil: Suarez, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina - Materia
-
4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINE
AIM
ATOMS-IN-MOLECULES
ATTRACTIVE H⋯H INTERACTION
BADER'S THEORY
CRYSTAL STRUCTURE
THEORETICAL CHARACTERIZATION - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
.jpg)
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/117864
Ver los metadatos del registro completo
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Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridineGranifo, JuanArévalo, BeatrizGaviño, RubénSuarez, SebastianBaggio, Ricardo Fortunato4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINEAIMATOMS-IN-MOLECULESATTRACTIVE H⋯H INTERACTIONBADER'S THEORYCRYSTAL STRUCTURETHEORETICAL CHARACTERIZATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/14′-Substituted derivatives of 2,2′:6′,2′′-terpyridine with N-containing heteroaromatic substituents, such as pyridyl groups, might be able to coordinate metal centres through the extra N-donor atom, in addition to the chelating terpyridine N atoms. The incorporation of these peripheral N-donor sites would also allow for the diversification of the types of noncovalent interactions present, such as hydrogen bonding and π-π stacking. The title compound, C24H16N4, consists of a 2,2′:6′,2′′-terpyridine nucleus (tpy), with a pendant isoquinoline group (isq) bound at the central pyridine (py) ring. The tpy nucleus deviates slightly from planarity, with interplanar angles between the lateral and central py rings in the range 2.24(7)-7.90(7)°, while the isq group is rotated significantly [by 46.57(6)°] out of this planar scheme, associated with a short Htpy⋯Hisq contact of 2.32Å. There are no strong noncovalent interactions in the structure, the main ones being of the π-π and C - H⋯π types, giving rise to columnar arrays along [001], further linked by C - H⋯N hydrogen bonds into a three-dimensional supramolecular structure. An Atoms In Molecules (AIM) analysis of the noncovalent interactions provided illuminating results, and while confirming the bonding character for all those interactions unquestionable from a geometrical point of view, it also provided answers for some cases where geometric parameters are not informative, in particular, the short Htpy⋯Hisq contact of 2.32Å to which AIM ascribed an attractive character.Fil: Granifo, Juan. Universidad de La Frontera; ChileFil: Arévalo, Beatriz. Universidad de La Frontera; ChileFil: Gaviño, Rubén. Universidad Nacional Autónoma de México; MéxicoFil: Suarez, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; ArgentinaFil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; ArgentinaInternational Union of Crystallography2016-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/117864Granifo, Juan; Arévalo, Beatriz; Gaviño, Rubén; Suarez, Sebastian; Baggio, Ricardo Fortunato; Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine; International Union of Crystallography; Acta Crystallographica Section C: Structural Chemistry; 72; 10-2016; 932-9382053-2296CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1107/S2053229616016533info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S2053229616016533info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:58:35Zoai:ri.conicet.gov.ar:11336/117864instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:58:35.624CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
| dc.title.none.fl_str_mv |
Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine |
| title |
Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine |
| spellingShingle |
Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine Granifo, Juan 4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINE AIM ATOMS-IN-MOLECULES ATTRACTIVE H⋯H INTERACTION BADER'S THEORY CRYSTAL STRUCTURE THEORETICAL CHARACTERIZATION |
| title_short |
Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine |
| title_full |
Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine |
| title_fullStr |
Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine |
| title_full_unstemmed |
Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine |
| title_sort |
Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine |
| dc.creator.none.fl_str_mv |
Granifo, Juan Arévalo, Beatriz Gaviño, Rubén Suarez, Sebastian Baggio, Ricardo Fortunato |
| author |
Granifo, Juan |
| author_facet |
Granifo, Juan Arévalo, Beatriz Gaviño, Rubén Suarez, Sebastian Baggio, Ricardo Fortunato |
| author_role |
author |
| author2 |
Arévalo, Beatriz Gaviño, Rubén Suarez, Sebastian Baggio, Ricardo Fortunato |
| author2_role |
author author author author |
| dc.subject.none.fl_str_mv |
4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINE AIM ATOMS-IN-MOLECULES ATTRACTIVE H⋯H INTERACTION BADER'S THEORY CRYSTAL STRUCTURE THEORETICAL CHARACTERIZATION |
| topic |
4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINE AIM ATOMS-IN-MOLECULES ATTRACTIVE H⋯H INTERACTION BADER'S THEORY CRYSTAL STRUCTURE THEORETICAL CHARACTERIZATION |
| purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| dc.description.none.fl_txt_mv |
4′-Substituted derivatives of 2,2′:6′,2′′-terpyridine with N-containing heteroaromatic substituents, such as pyridyl groups, might be able to coordinate metal centres through the extra N-donor atom, in addition to the chelating terpyridine N atoms. The incorporation of these peripheral N-donor sites would also allow for the diversification of the types of noncovalent interactions present, such as hydrogen bonding and π-π stacking. The title compound, C24H16N4, consists of a 2,2′:6′,2′′-terpyridine nucleus (tpy), with a pendant isoquinoline group (isq) bound at the central pyridine (py) ring. The tpy nucleus deviates slightly from planarity, with interplanar angles between the lateral and central py rings in the range 2.24(7)-7.90(7)°, while the isq group is rotated significantly [by 46.57(6)°] out of this planar scheme, associated with a short Htpy⋯Hisq contact of 2.32Å. There are no strong noncovalent interactions in the structure, the main ones being of the π-π and C - H⋯π types, giving rise to columnar arrays along [001], further linked by C - H⋯N hydrogen bonds into a three-dimensional supramolecular structure. An Atoms In Molecules (AIM) analysis of the noncovalent interactions provided illuminating results, and while confirming the bonding character for all those interactions unquestionable from a geometrical point of view, it also provided answers for some cases where geometric parameters are not informative, in particular, the short Htpy⋯Hisq contact of 2.32Å to which AIM ascribed an attractive character. Fil: Granifo, Juan. Universidad de La Frontera; Chile Fil: Arévalo, Beatriz. Universidad de La Frontera; Chile Fil: Gaviño, Rubén. Universidad Nacional Autónoma de México; México Fil: Suarez, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina |
| description |
4′-Substituted derivatives of 2,2′:6′,2′′-terpyridine with N-containing heteroaromatic substituents, such as pyridyl groups, might be able to coordinate metal centres through the extra N-donor atom, in addition to the chelating terpyridine N atoms. The incorporation of these peripheral N-donor sites would also allow for the diversification of the types of noncovalent interactions present, such as hydrogen bonding and π-π stacking. The title compound, C24H16N4, consists of a 2,2′:6′,2′′-terpyridine nucleus (tpy), with a pendant isoquinoline group (isq) bound at the central pyridine (py) ring. The tpy nucleus deviates slightly from planarity, with interplanar angles between the lateral and central py rings in the range 2.24(7)-7.90(7)°, while the isq group is rotated significantly [by 46.57(6)°] out of this planar scheme, associated with a short Htpy⋯Hisq contact of 2.32Å. There are no strong noncovalent interactions in the structure, the main ones being of the π-π and C - H⋯π types, giving rise to columnar arrays along [001], further linked by C - H⋯N hydrogen bonds into a three-dimensional supramolecular structure. An Atoms In Molecules (AIM) analysis of the noncovalent interactions provided illuminating results, and while confirming the bonding character for all those interactions unquestionable from a geometrical point of view, it also provided answers for some cases where geometric parameters are not informative, in particular, the short Htpy⋯Hisq contact of 2.32Å to which AIM ascribed an attractive character. |
| publishDate |
2016 |
| dc.date.none.fl_str_mv |
2016-10 |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion 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://hdl.handle.net/11336/117864 Granifo, Juan; Arévalo, Beatriz; Gaviño, Rubén; Suarez, Sebastian; Baggio, Ricardo Fortunato; Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine; International Union of Crystallography; Acta Crystallographica Section C: Structural Chemistry; 72; 10-2016; 932-938 2053-2296 CONICET Digital CONICET |
| url |
http://hdl.handle.net/11336/117864 |
| identifier_str_mv |
Granifo, Juan; Arévalo, Beatriz; Gaviño, Rubén; Suarez, Sebastian; Baggio, Ricardo Fortunato; Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine; International Union of Crystallography; Acta Crystallographica Section C: Structural Chemistry; 72; 10-2016; 932-938 2053-2296 CONICET Digital CONICET |
| dc.language.none.fl_str_mv |
eng |
| language |
eng |
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info:eu-repo/semantics/altIdentifier/doi/10.1107/S2053229616016533 info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S2053229616016533 |
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info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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openAccess |
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https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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application/pdf application/pdf |
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International Union of Crystallography |
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International Union of Crystallography |
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CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
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dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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